So fare I have received stretches of silence when I asked that question.

The two apartments will bring in $1900 monthly.Is it a stretch to list this house at $100/foot and hope to get $90/foot?

It could potentially work pretty well in convincing the seller to stretch those payments out further.   

Excluding your taxes and insurance, there are two things that determine your monthly payment for a given dollar amount borrowed:  Interest rate and length of time to repay the loan.In your current situation, assuming that your interest rate does not change at all, you are simply stretching out the mortgage payments for a new 30 year term.  

Now you know why so many investor buy property out of state as the dollar and cash return stretches much farther on average.You can be passive with commercial but quality assets on your own have you putting down a minimum of 750k to 1 million or more.

If your budget will stretch to it initially, once you've found an investor friendly Realtor, Lawyer & CPA, (maybe a bookkeeper/financial planner too) - get them together in the same room, and talk through your goals over the next 6-12 months.It sounds extravagant, but you'll be AMAZED what comes out of sessions like this, and it often provides an insight as to how to get started and in which direction. 

Cloud to Kissimmee area (willing to stretch to Lakeland). 

You may be able to take out an unsecured working capital line of credit in a business entity name that will not report to your personal credit report, but in the 10's of thousands with no prior relevant experience is probably a stretch.

I find myself trying to justify the valuation and needing to stretch the am schedule out on our seller-carry to 40 years to break even monthly.  

hauling,  unrollingunrolling,  scraping walls,  stretching,  etc...