I am contemplating selling it, but there is an 1100 SF shop (garage) attached with a MIL apt above it (approx 950SF with kitchen, full bath and 3 other rooms) that has a separate entrance.

I just started contemplating about being a real estate investor about 2 months ago.

I keep contemplating whether of not its smarter to keep or sell with such a high HOA that will only increase.

@Don Carey Oh ok, my mistake, when you said move away from SFR, I was under the impression you were contemplating unloading those properties and moving that money to more multifamily. 

Contemplating on whether to level the house and fix land grading/drainage issues which may end up costing $20K and doing some cosmetic updates or whether just to leave the house as is and do cosmetic fixes and just disclose to buyer that it is not level. 

I am contemplating selling the home and using the proceeds for a 1031 exchange whereby she would purchase a condo to live in, and another condo for rental income.

And makes sense after reading your response that active investment (as I was contemplating) would be treated differently from a tax perspective.. 

I want to stay away from Section 8 for now.As for NY, I've contemplated Poughkeepsie, but I'm not too fond of how the job market/population has been looking. 

First SFR deal is getting closer and closer, I have it narrowed down to 2 and now I am contemplating how I am paying for it.  

I was contemplating if I should use the cash to pay off or reinvest.