You're far better off finding a market that fits your goals than to sub optimize your investment from the start.

If the seller sells after 365 days, it is long term capital gains, unless the seller lived in the property 2 of the last 5 years, then there is no capital gains.A good example of optimal tax write offs and profitability is in the following spreadsheet.

Some good lists to target are Absentee Owners with Equity, Seniors with Long-time Ownership and Homeowners with Low Financial Stability Scores.You can work with a list broker to optimize your list for your area.

Always fascinating what happens when you artificially control supply and demand, it leaks out somewhere because people will always find a way to optimize their situation, whether the landlord or the tenant, as you point out.

To make sure your website is set up to convert visitors, consider this conversion optimization checklist (link in original article).House Seller Real Estate Statistics The median price for houses listed in the U.S. is $254,900. 

But it is usually a less optimal solution. 

You had enough risk margin to absorb a loan that may not be optimal, and you have already learned a few lessons. 

Rent larger home, use cash to rent a smaller home/move to retirement community (disadvantage: less community of older folks; advantage is we can continue to own the home but make money off of the rent payments; but now we have to manage new renters)Basically asking if anyone has experience moving to a retirement community, and what the optimal move is with our current real estate assets.Where could we talk to similar people in this situation?

ARV about $180-195k My optimal strategy would be to rent it out to students $400 a room.

Are you planning on keeping the complex or flipping it once optimized?