I will be revising our application to make it more fool-proof and will be setting rules for what dictates auto-rejection to save us time.

Tenants don’t dictate what updates, repairs, or improvements will be done by the landlord during the tenant’s occupancy.Good luck with this tenant.

Hi Jose,I'll answer the question I think you're asking vs exactly what you wrote.Larger than 4 unit Investment property takes typically 20% down, plus closing costs, and possibly attorney fees.You will probably need cash reserves (as dictated by the lender) and to pay for specific fix ups by a certain date after the closing date (as dictated by the lender and possibly the insurance company) in addition to any improvements you intend to make.Roof age can make lenders balk at lending--so pay attention to that.

This isn't always true, but in this area, where the military BAH dictates a lot of the rental prices and it's a very heavy vacation hot spot, the STR is generally a stronger play.  

@Masa MoromisatoShorten the distance, if you need you have cash now, a MF syndication can be a good outlet it would mitigate your need to get financing, banks right now will only tighten the belt in the coming months, you have a high risk for just buying 1 or 2 houses for cash, depending on the markets you looking at it will dictate if you buying for cash flow or appreciation (Midwest Is a good consistent cash flow machine with limited value volotility)If you are looking for a steady return a syndication deal may be an excellent avenue and all you to build back some strength in lending and capital in the mean time.PM me any further questions

That's not to say that the past will dictate how the market will act in your area but its data you can use to help guide your decisions. 

Since we bought REO, seller, which was the bank, dictated title co, and they were not great.Second one was an unrecorded death certificate, to clean up chain of title and take a spouse off. 

The answers to all of those should dictate the answer to your question.

It is the landlords obligation to pay the interest dictated.

The laws in your area and your CCRs will dictate what can/cannot be done.