I've been toying with the idea of getting into rentals as some more supplemental income, and although I've struggled with the math as far as justification, i believe the main reasons folks here by rentals (please correct if I'm wrong) are: Cashflow (although I've seen people do deals eg on Roofstock for only $100-200/mo) + appreciation (when sold) + taxesSo assuming I'm correct there, then the potential tax benefits are 30% of the reason to do rentals.

-seller has the ability to foreclose on you and keep the payments you've made to that point (and the property he would potentially be repossessing would be totally upgraded on your dime-seller receives steady passive income which may be very attractive to someone that ageAs far as other leverage, the most important thing to do would be to find out more about HIS needs. 

I’ve always get stuck at this stage, I don’t want it to go away because it’s a potential deal I believe.

My philosophy is if you buy right and are conservative with your numbers, what happens to the market on a macro level is less important because you have protected yourself against a potential "crash".

It seems to me that you are potentially missing out on the tax advantage of living in your flip. 

You can get potential cash buyers.

I know the area somewhat due to growing up just across the river in the Poconos but would love to work with someone that knows the areas potential and can help find deals.

I am getting married in November and promised my fiance that I would focus on RE education until then...My question is, is it too late to BRRRR this property and use the funds to repay my family member/potentially buy my next income property after I get married?

For sellers who do not know the process well, any of these can become problematic, and if you've left yourself unprotected in the contract, potentially costly. 

I like the cash flow potential of this propertyHow big of an obstacle would this be?