It depends on their business model. I have experienced some apps
a) just add on user base so that they can monetize the app as an asset . So they do not charge anything for the app or within the app
b) Some use advertisements within the app

There are Pros and Cons for both the approaches . Build vs Buy is always a decision that requires considerable moderation

I am assuming that you are just starting your business , so with this assumption the following pointers may help
a) what is the value add you bring with your job board
b) what is the differential your job board will bring as compared to other job boards in the market

So you have to weigh in against the following
for Buy / reuse : no maintenance, can avail support , to some extent less effort and hence less cost
but then you will have a generic job board , duplicate of other job boards
For Build : Specific to your values,unique to represent your differential
cons: maintenance, support, cost and may be time to market

we can discuss this in detail if you like

For the last 15 years I have been engaged in pricing IT services and products. Monetization of app is a y product of building a business plan for your services. we can connect for developing a business plan based on
a) Your costs for development of the app
b) your regular cost going forward in enhancing and maintaining the app
c) user base target of your app
d) building a revenue model that will ensure sustenance and growth

There are two streams in your own words
a) You want to increase price per unit of your time
b) You want to monetize freebies
However from the words above I understood that the justification of increasing price is the new site that will have additional expenses to maintain.
I am also assuming you business is to providing services

Increasing the price based on the changes in site can only be so much ( means very little) depending on how important
for your customers is visiting of the site. Services business is more of Word of Mouth spread and repeat customers do not tend to value up scaling of sites much. If your customers come to your site to avail / buy services then upscaling of the site can be redeemed to some extent. This extent is limited to
a) either increase in value the customer gets from the services ( in your case None)
b) customer perceives additional costs / inflation : This is more applicable to you however the increase is limited to inflation factor only (1-2% in developed countries)
So I my suggestion to increase the rate (per unit of time) can be equal to Two inflation cycles (e.g combined inflation of 2 years)

However your biggest monetization is Freebies. this is where you have the scope and this can be based on Freebie or based on Unit of time. We can discuss Freebies and their monetization if you like

Though it is the buyer's primary responsibility to verify and validate for trademark infringements, however this does not waive all your liabilities.
If the domain names are violating any trademarks before sale, then you would be accountable too for that extent
You will be liable for damages and claims for any infringements till the time of the sale

Market research is a big ocean in itself .
What will be acceptable to the investors :
a) Primary Research (market size, market segment, customers behavior, product costs, profits, competition etc )

b) Secondary research from public and commercial sources (market size, market segment, customer needs / wants/ desires, current players in the market, concentration of the players etc)

You should be able to reconcile the differences in the two research methods ( e.g Primary research market size may differ from Secondary research market size. Which one is more realistic you should be able to understand the differences and align your proposal accordingly )

I think Yes these would be acceptable to the investors or say
that these are the minimum things that investors will seek from you

However What will attract investors to your proposal are the following things
a) Profit potential ( be prepared with cash flows, income statement, balance sheet simulation ) for next 5-10 years, you should be aware of financial ratios , break even analysis

b) Your own beliefs in the product ( what is USP of the product, what will make it sell, what will drive profits)

c) your commitment levels
(your role and your own evolution as the product grows)

d) your depth of research or knowledge of the market and product
(Yes primary and secondary research )

Feel free to reach me for any support and help

yes you should ask for this money because this will be your liability
These customers are entitled for unconsumed part of the year if you close down the gym, however if you plan to continue running the gym (whatever name) then you are liable to provide these customers services till their year completes

It is a good question if the growth of the company is well structured defined and firm or it is dynamic to mirror the growth.
The growth path is generally on the lines of the focus the leadership has in this growth period. If the leadership is focused on results the evolution of a growing tech consulting company is casual, dynamic and result oriented. The staff will be performing multiple roles and the org structure would be lean

However if the leadership is focused on performance and process oriented, then there is likely to be hierarchy ( whether it is projectised or matrixed or could be hybrid) .

Whatever is the focus however this would be the right time to bring formalization in the processes and results.

There are many Task management software in the market, some very targeted towards the task delivery approach (Waterfall, Agile etc)
MS Project, Clarity, Clarizen, HP PPM are typical waterfall based software
Rally, JIRA, VersionOne, Asana, Smartsheets, etc for Agile

Question for you : Is it just the Task Management or are you looking for everything related to tasks (duration ,effort, resources etc). Based on the requirement exact software can be recommended

Process evolution at startup is always a challenge.
Your current team (one developer and 2 advisors) is in actual one member team ( I am assuming that advisors are not doing any technical software development)
Formal SDLC approach will be a challenge and it will always be for this software developer to juggle
a) New feature / functionality development
b) Defect resolution from past year release
c) Any incident , defect or change in the past year release
My suggestion would be to build an ServiceDesk like item log ( divided into three categories above) and prioritize for the developer in consultation with manager and technical advisor.