We were on a very quick timeline and were able to get one quote that didn't seem too bad, but we still were concerned about future resale value.

I would give them a list of what you’re looking for/at ahead of time and obviously not linger in areas where this couldn’t be a concern.

My posts aren't specifically about Rent to Retirement, rather the concept more generally.I am also not concerned with the new construction turn key model, its very different than the lower tier/entry level SFH's and not relevant.

That is one concern, but the current tenants have been there for a long time. 

While the prices are attractive, I'm concerned with its long term viability.

My other concern is that home prices on Long Island appreciate quickly.

Your concerns are valid, and it's clear you value both guest experience and neighborhood harmony.Given that a minor increase in guests might not significantly boost your rates, maintaining the current plan seems wise.

Not too concerned with rent/price ratio on single family homes since none of them are really going to cash flow a ton anyhow unless they are paid off. 

I'm concerned that this will not get resolved and I am just being strung along at this point.Are these type of issues common? 

THEN, I plan to purchase the second home using a FHA or conventional loan (3%-5% down), for which I will likely pay the monthly cost out-of-pocket, maybe with some rental income support if it is a duplex.My concern is, I do not want to spend my savings or weigh down my debt-to-income ratio so much so that I cannot qualify for and pay the down payment and closing for the lending on the second home.Questions: - With the first home being multi-family, 75% of the rental income (or potential rental income initially) will relatively either maintain or boost my debt-to-income ratio from lenders' perspectives, right?