I'd say to start with an informal, small gathering, see what the participants are interested in, and then plan the next one based off of their feedback.

Try an asset based lender for a short-ish term (3 years usually).rate will be higher, but it'll be an easy loan to get with almost no underwriting.

I kinda agree with @Larry T. there is presently a storefront vacant building right at the corner of where i leave, the store is rented out but the apartment is vacant and it has been like that for at least 2yrs.You also need to be wary of the location, correct me if i am wrong but buildings were there are apartments and stores are technically in D, E locations which could have a lot of issues. this is based on my drive and stay in Rochester NY.Your located in NYC, i think you could take a day or weekend off to come down here and check the neighborhood out.

@Michaelmy apologies some times it takes me a little bit to answereasiest way to explain formula for youArv is After Repair Value meaning after full renovation or repairs this is what the house will sell for 30-60 days max based on comparable sales (aka comps)I prefer lower 60% of the ARV, because I prefer to flip to a retailer, by wholesaling, and earning a small fee for finding the deal and securing the property via purchase agreement option or a few other various formsmost of my ppl buy at 65% or 70% so due to my preferred method of wholesaling, I must buy at prices below these "strike prices" or buy prices...just so you know I am a contractor, so my repair costs are known when I look at property.

So based on my brief description of my background, would you all say I'm ready to take the risk on my own, or would it still be highly advised to work directly with someone who is currently successful at doing so?

This may not be a big deal to a rural based farming family, but it can be a big deal for a commuting family.  

Based on your original paragraph you need to raise rent and/or remodel so you can raise rents.

(This is all based on my anecdotal experience).

I'd be able to cover the loan payment based on what I'm typically offered for a housing allowance.

I've never had an issue splitting the utilities based on RUBS and getting paid after billing them quarterly.