I was debt free, but thanks to the lessons learned from the hurdles I encountered getting to this point I understood that I still wasn't truly "free."

yes l try to learn something from each and every deal or encounter that l come across or am involved in (ln life)....Thats great wisdom my friend!!.....

What is strange is she pulled up the comps and they were almost 50k more than what he told me... so either his construction company is going to do a really awful job on the repairs lol or he's somehow (I'm not sure how) trying to scam on that end too.

He is 100% a scam.

Being that I am young and wanting to get into investing in rental properties, what are some hurdles that you think I may encounter that I can be better prepared for?

It was very stressful as the Seller reiterated over and over that we needed to close in 30 days - Ultimately, I believe we did it in about 30 days all things considered.While going through the inspection, the Inspector noted that there were structural issues -*For those starting out, if you encounter this I would strongly recommend that you stay away from this type of issue unless you're very educated on how to resolve these issues cheaply and timely*We budgeted another $20k into the 203k loan to resolve these issues and proceeded to close...Our Consultant recommended a Contractor that he had worked with numerous times using the 203k loan and we honestly could not find someone that wanted to charge a reasonable price and work with the 203k loan so I spoke with the referred Contractor and accepted his bid.Note: While you should take referrals into consideration, I would strongly recommend that you shop your Contractor in advance before putting a property under contract.

Trying cash for keys and other tactics it was day in court and $7500 to convince the owner to leave after 3 months.Has anyone encounter this situation and how was it resolved. 

Maybe some of you have encountered similar situationsMy worry is that it may not be in my best interest to contact lender.

I would never cut a wholesaler out if they brought me a deal, but I am very suspicious of any wholesaler and their deal when I do encounter them. 

So I've been trying to setup some bridge stuff lately and running into lots and lots (and lots and lots and lots) of obvious scams.