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.

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

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

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? 

The concern with the DSCR loan is that I need to make the property present as though it's rented to individuals during appraisal (tough since it's a working rehab facility now) and must create another lease that shows the tenant as personal and not a company.

If you tell the constable that you are concerned about damage, they may talk to him about leaving responsibly.If you are concerned about violence, have a means of defending yourself and let him know it.