With your desired price point, the Midwest is going to be your best bet.

I was almost positive that because Orlando is such a desirable area that investment props will probably go pretty fast so yeahh that just confirmed my expectations.

It will also allow us to sell off one or more lots if desired, to finance the next steps of engineering in prep for construction.There is a cost to subdividing, so we are trying to think about the return on our money.  

Content to live quietly under the radar & continue buying, we've never had the desire to own a Lambo etc.

These would be C- (at best) or D neighborhoods that many potential guests would not find desirable - especially when there are really great, fairly priced short-term rentals in good A and B neighborhoods.

I own a company that purchases high end cars such as the Tesla S's, then rents at a consistent and predictable pricing to self-starting business owners desiring supplemental income through Uber, chauffeur services, and shuttle services.You could consider using a service that provides you this the same. 

Quick background on each member:Parent: Has plenty of capital and wants to invest it; does not have the desire to be out finding deals, financing, rehabbing, etc. and lives in a small market with minimal real estate activitySibling: Has limited capital, time is somewhat tied up in multiple endeavors though sibling does want to provide some help in the day-to-day as time allows.

This proposal will obviously make buying your home less desirable since you either take the Standard Deduction or you take an Itemized Deduction, which includes Mortgage Interest on your Primary Home.All in All............... this is sounding DISASTROUS toward Real Estate in general.I think for those of us who are in route to financial independence, these are two road blocks which have been put out there for us to navigate through.In my mind, 3 questions come up.1) Did I misinterpret the Republican Tax Reform correctly with these two rules?

What mindset and skills are desired in this Market in order to network efficiently and benefit all parties involved?

Comps with 3/2 are renting for about 1350 in strongly desired neighborhoods.