The condition of the house is pretty bad, ceilings are really low (i am 5'10), floor seems uneven,  entire house needs new flooring, new bathroom, kitchen, patio deck is warped.

Prohibited in all states is the refusal to rent because of ethnic background, race, religion, sex, sexual proclivity, age, marital status, or income source. 

(I am wondering if sending from my own account somehow makes it a prohibited transaction.)Anyone have any good advice about how to resolve this cleanly?

Also, let’s say I find a deal that may look interesting (by looking at the physical condition of the property), how do I figure out the costs such as insuranse, garbage/sewer, water etc?

Another lesson learned here is to make sure that the security deposit is a sufficient amount (many get a full month's rent) and have it stated in writing that the security deposit is non-refundable, but gets converted to a refundable type once certain conditions are met.  

I may be forced to just leave my portfolio alone which by no means is a bad thing for me, unfortunately our DTI prohibits us from acquiring more SFH, so therefore by default i will have to scale up and purchase multi family buildings outside of NY, this may not be a bad thing either.Ideally, i would love a BCB to give me a blanket loan on my SFH and therefore freeing up our credit to purchase more with conv residential financing.Leo

However,Depending on the roof condition there may be more options.

I am a new landlord and rented my property 1x so far for 6 months to someone I know and work with that did not turn out well at all - I was completely scammed I convinced him into leaving my property without going through the eviction process and he took care of the house as in keeping it in good condition. 

@Chuck King / @Justice CannieIf you're buying distressed and fixing them up to add value then you can achieve up to 2% rent-to-value ratios based on your cost basis.If you're buying in like-new condition (little to no renovations) then your rent-to-value ratios will be lower, often around 1% in the right areas and in balanced markets.Keep in mind that all of the above is a scale that is highly market dependent.Continued success!

I just recently found out that the air conditioning condenser unit may need to be replaced at one of the properties I bought a few months ago.