There are two conflicting thoughts here, to me:-One says that you are limiting the number of people interested in the condo because they won't be able to rent it out, thus lowering the prospect pool and price.

The tenant has been paying significantly lower rent for quite some time, approximately $200-300 below market price for a similar unit.

We have one roommate living with us.My thoughts are to remodel the current house add a master suite to the bottom of our split level foyer.

This is the level of how most homes are being rehabbed.

What happens if: the rehab costs more than expected, the flip is delayed or the sales price is lower than expected?

I have focused on minimizing my expenses so that my "financial freedom" number is lower. 

The GCs and builders would rather play at the subdivision level than a single property/parcel.

It can cause complications at the buyers bank when they go to figure at the purchase price (it may be lower than the option price by the amount of the fees).  

They are overseas group of investors purchasing with cash, so they should be good on that front. it will likely be more on the lower end of the range.If anyone has some tips or a link to a good article/blog to check, that would be great.I'm going to do a lot of due diligence obviously, but just wanting to get some opinions from people here that are experts in this.

The second loan would be a 30-year fixed lower interest asset-based non-recourse loan.