If you were starting out what would route would you choose given your own personal advantages? 

Thanks to both Dan and Jesse for the response - definitely thinking that now is the time to take advantage of lower jumbo rates, so long as I can get a good enough comps for the appraisal, since that'll be the key deciding factor of refinancing here.

Just curious how you would handle as I believe I’m being taken advantage of.

Some wholesalers may take advantage of a new investor and if you back out of the deal with one, you will likely lose your earnest money deposit, usually $5K.Because the FIRST investment deal is so crucial (if it goes well you will most definitely continue your REI journey, if it goes badly you may never want to buy another investment property) I suggest that you first spend a good amount of time (3-6 months or even longer) to educate yourself on how to become a successful real estate investor in the particular niche (house hack, BRRRR, single family, multi-family, wholesale, flip…) that you will pursue. 

I get use technology to my advantage.

She was taken advantage of after suffering home damage during Hurricane Harvey (2017) and lost almost all of her savings.

I was also really lucky to meet some really helpful local investors in Indy through BP, and quite frankly it sounds like @Nick Giulioni has a lot more local knowledge than I would and I'd definitely take advantage of that if I were you! 

@Jermaine Martin -  @Victor So mentioned some good options, but if you have lived in the house for the last 2 out of 5 years I'd take advantage of that and pay zero capital gains!

If your roof was at end of life, I would agree that there is some advantage to getting the new roof rolled into your long term financing with the small side benefit of MAYBE a little higher value on the home.

It gives me an advantage if I can  purchase all cash at rates less than 50% of hard money (some people do the same thing with life insurance or lower risk investment options).