I have contractor/construction experience (20+ yrs) and am currently a licensed Real Estate Broker. 

I’ve had Geovera for 3 yrs and just got my renewal, wind only, and the premium jumped from $1560 to $2650 for the year.  

My current monthly mortgage is $1978 (8 yrs remaining for 15 yrs refinance) and $1300/mo needs to be allocated for property tax.The problem I have is if I lease the house with current mortgage payment, I would not make any positive cash flow due to higher monthly payment and high property tax rate 3.15% (Yes, it is Texas).According to the local realtor's rental comp, the rent for my house would ranges from $3100-3600.

Planning to buy my first invest prop in a couple of yrs. 

My dream for 20 yrs, is to invest in multi family housing, but life gets in the way. 

But I also know that we won't have the money to pay to fill in the gap when we go to sell in 5 yrs.  

I'm evaluating a portfolio of 40+ section 8 SFHs in C/D neighborhoods in a tertiary market, all of which are 50+ yrs old.  

That spread will most likely narrow as Chicago has already passed a series of property tax hikes which will be phased in over next few yrs.  

I will only benefit from the $300 monthly cash flow over 10-15 yrs and the two payments (one when I buy the house and one when I transfer it to his name).

   I found myself in the same boat 3-4 yrs ago, and decided to go with an hybrid approach.