People can deal with a 5% increase (in this case 100-150), but a 10-20% increase is more likely to bump them out.Also remember that you have to hedge against future markets in which you will not be able to increase rents. 

Have them take you through the whole financial process to see how they determine the metrics and how they assess projects. 

I will be relocating to NE Florida in the near future and looking forward to joining RE groups and meets.

He is aware his capital gains tax will be higher when he ends up fixing and selling the property in the future. 

They take these complaints seriously usually and will be able to more than likely take this contractors license away so they don't do this to future investors!

past performance does not guarantee future results.

Definitely want to get into development in the future of tiny homes, multifamily, etc.

Purchased for kids future/college fund (maybe relevant maybe not) Mortgage rate is 4.4% currently paying $1149 a month (including taxes/Insurance)Currently rents for $1550 (room for upping rent to $1600+)In the 2 years Ive had it, Ive added a roof(insurance claim),new windows, new bathroom, plumbing.

I would guess that in the future you would qualify.Also, your math is a bit off above but I wouldn't really worry about it.  

Look at population/migration trends and futures.