I view them as a business that I want to keep in business, I would not get their rental rate from a normal tenant but I don’t really want to share the volatility of the pricing until I can evaluate how capable of a host they are.

Here are some preliminary numbers I ran: 260K FHA no repairs and current rents on left, 300K 203K, reno and higher rents on right: % Down Payment 5.00% 5.00% Down Payment $13,000 $15,000 Remainder of closing costs $3,000.00 $3,000.00 Total Due at Signing $16,000 $18,000            Mortgage Rate 4.60% 4.60% Length of Mortgage in years 30 30 Monthly Mortgage payment $1,266.00 $1,461.00 Taxes $386.00 $445.00 Sewer and Water $50.00 $50.00 Trash $50.00 $50.00 Heat/Utilities $ - $ - PMI $ 180.00 $ 208.00 Cap Ex and Ops $200.00 $200.00 Insurance $65.00 $75.00 Mgmt Fee $165.00 $165.00 Vacancy $132.00 $132.00 Total Expenses $2,494.00 $2,786.00     Unit 1 $500.00 $700.00 Unit 2 $900.00 $1,100.00     Total Revenue $1,400.00 $1,800.00     Cashflow/month ($1,094.00) ($986.00) Cashflow/year ($13,128.00) ($11,832.00) Cash on Cash Return -8.42% -6.57% I have not talked with the seller in detail yet, as I want to see if this is worth a deeper dive first. 

Details of who is responsible for what. 

For some reason, I have the idea of putting together a detailed binder of my plan, markets I'm eyeing, different number projections and scenarios, etc. and understanding that binder backwards and forwards and pitching the plan to potential lenders.Is there some kind of 'checklist' of documents, figures, etc. that I can refer to in order to make sure I have everything on hand that I might need when addressing lenders' concerns and questions, in order to convince them on my plan?

Ok a little more details.

Is there any ways I can have the property listed now and have schedule viewing for future prospective tenant?

Also make sure everything is always in writing and very detailed so there are no questions if anything ends up in a dispute. 

The condition we typically use allows for a concession of 3-months scheduled rent if a unit becomes vacant between the acceptance of our offer and Close.That said, when you collect estoppels during diligence, most "irregularities" between information supplied by the Vendor and the tenants' views will be exposed and you can simply negotiate a resolution at that time.

Any insight or advice would be greatly appreciated, I can send more details of the projects as well. 

@Arbi Boghoz - I just helped another investor with a rental just steps from MacDill, I will send you a PM and we can chat in more detail.