Some renters may hesitate, but if the rental market is strong and insurance is covered in your numbers, it can still work.

the 50% rule doesn't know roof age, individual market dynamics, anything about utilities, etc. 

I’m pretty busy with my job as it’s a 24/7 industry, I don’t have time to handle aggressively hunting for off market deals however I could still do it with mailers, as I’m in no rush to purchase right away.

You may want to get in touch with @Sharon Vornholt who has done a lot of marketing in this niche.

You cannot choose a section 8 tenant over a market rate tenant.

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Has anyone here been successful in permitting a conversion?

I immediately recognized that the listing agent/property manager had the current rent well below market & the asking price massively wrong.

I'm not too familiar with the markets yet but research I've done suggests that the towns of New Britain, New Haven and Hartford all have a good mix of inventory and low prices coupled with plenty of amenities, night life, cafes, etc and local colleges to bring younger people to the area year after year.

Raw land is tricky for even experienced agents/brokers to sell.Co-marketing a vacant lot with a builder is not a new concept and is done frequently.