Cold Calls - I find this extremely draining and it comes out when I do call.

Trouble is, this quote is over 10k more than the initial quote.

This is a different situation when residential properties are sold.

He has 3 months of rent left and this is for 1 year new contract.

This can provide you with a low-stress introduction to real estate investing.

I am sending contractors to give me an idea of what it would take, but wondering if someone on bg has already done it and has advice in this regard.

You might have done this already but maybe calling some agents there or finding property management companies in that area? 

Your realtor isn't just there to open doors; they're your guide in this new world.

If this was your first year getting a 1099, then there might be a small chance that you could get away with just this year's 1099.....HOWEVER, since you have been 1099'd for 2 years now, then the mortgage lender may request tax returns before extending a mortgage. 

With so many local investors responding to this post, maybe we should do a BiggerPockets Meet Up here in Daytona.