I find it smart to be cautious but debilitating to be scared.

Many companies were burned hard in the last cycle, so everyone is being cautious.

On BP those starting out talk about leverage to get scale.. this must be done cautiously in my mind.

one benefit of INDY over Memphis is double taxation.. if you own property in the city of Memphis you pay city tax and county tax .. so one must be very cautious of this.. as property tax's are one thing you can't mitigate with better management better properties etc.And for a shameless plug on Brie's site you can take properties from each market ( since we are talking one VS the other) and plug them in side by side and compare the operating expenses from each and draw your own conclusion. one of the great things of turn key reviews.. this is were you can find some good numbers to make your comparisons when your talking one markets over another.However its still my humble opinion as one who has worked almost all the Turn key markets that they are somewhat interchangeable.. simply because the PP to rent ratios are about the same. and the renter demographic is the same.. so it comes down to the team.. that will manage your tenant base. 

I'm concerned we're being too cautious by not jumping in the deep end and buying a live-in flip.

Personally I would be cautious about investing in 2nds, WHEN we have the next recession we will know how well these hold up in a tough market.  

Kissimmee is the most competitive STR market in the USA so unless that property can beat the 100 nearest properties near you with regard to design, finishes, amenities, etc I would stay very cautious. 

But the -population growth, -job growth, and mostly manufacturing elements of Detroit, all have me feeling cautious.

If your income is also coming from real estate profits you'll need to be cautious on how you list this income.

If this is a FT job supporting a family not PT do a few deals, I will be very cautious wanting to understand the outcome.