The other aspect to consider is how long you have been friends.

If the Association is well run, major expenses are generously accrued for, and there are no onerous rental restrictions, I wouldn’t be concerned about that aspect.

Only you can really answer what aspects you prefer.

We found ESS to fall short at random aspects of parking vehicles, it is clear they are designed for enclosed units.

We're fortunate to have worked together for many years and so going into this new venture I think we have a pretty good idea about who might be better at certain aspects of the business. 

Yes, there are definitely ways to get in real estate without capital, but don't ignore that aspect of it.  

So, take what you've got from that last era and the years since, and try to leverage that to help the people in your market who have the other aspects down. 

Some things about banks and loansDownpayment 15%-20%, for you it will probably be 20% required as you have no historyLoan costs will be about 3%-7% of the total loanThey will analyze every aspect of your financial history including past residences, employment, reserves, spending over the last 6 months, tax returns over the past 2 years, all bank accounts with your name attached to them, income statements.For a $100,000 home expect the bank to want to see $30,000 in your account (20% down, 5% loan cost, then an extra $5,000 for reserves)So while it is possible for your to get a loan, expect to jump through a lot of hoops.

We haven't figured out a niche yet, but we are exploring all aspects to see what sticks in our local market.

Then from an appraiser aspect, I would probably go ahead and see if you can chat with a local appraiser and see what they say.