My biggest fear is that if I ever were to quit my job, I would no longer be able to invest in more real estate (not sure if I would qualify for loans as easily). 

You can do some really cool, unique, and creative designs with containers.Do seniors want to build/buy in a rural area vs city area? 

As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

In some very attractive markets like coastal cities I can see it being worth it not to rent the unit or rent it only under very limited circumstances in the low season because the high season is just too lucrative to allow anything to affect those bookings.

The biggest advantage of using someone local to where you're buying is that they will understand taxes, insurance, and similar items very well when it comes to DTI/DSCR calculations and payment quotes, and they will likely have a local network of service providers for ancillary services (survey, inspections, etc).

Hey @Matthew Ferguson ...That depends if you're thinking of going the LTR route in the city of St.

Hey all, I'm Stanley from Oklahoma City.

The prices are still really affordable compared to other cities, but you get solid rental income potential.

It has sat empty for the last 20 years but the current owners have completely gutted it, have bids from contractors they're willing to share, cost estimates etc. and have had lots of inspections done and so much pre-work with the city and county to figure out what they can and can't do, so a solid plan is already in place.

I think one of the biggest risks you face with Cash Out is interest rate risk.It's really difficult to predict where interest rates will be in a 2-5 year time period, so it can also be challenging to model out future mortgage rates.