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.

Hi Alexander Owen, yes, to being able to buy the next property using FHA, but they will want you to refinance the MassHousing loan into a conventional product first.I actually used the exact strategy you are contemplating to start my empire 3 years ago.

however, the reason I was contemplating was I did not know if I have to up potentially pay $3500.00 (loan origination fee and everything to finalize the loan for the closing and ended up with buying the property).basically, I did not want to pay $3500.00 to get the loan of $20K vs. pay a smaller fee to get the HELOC which I could potentially lose this deal due to longer time to get it approve. 

And by a small operator, I am referring to contemplating getting started and researching whether this could be a viable and legally acceptable strategy for an individual looking to do a few deals a year, but potentially exceeding the magic state set number for private sales.

I just purchased a SFR in Bonita Springs / Naples (SWFL) area and am contemplating whether to rent it as a short term vs a long term rental.