Quite often, wholesaler A sends me a property and a few days later, wholesaler B sends me the same property but with a slightly increased price (including his fee).

Then start doing flips, buying notes, tax liens, and more to help increase your capital while the rentals provide a foundation to rely on in case a fix and flip goes bad.By the way if you plan on managing the property yourself, try using a service like cozy.co or something similar.  

Fifteen year lease with annual rent increases and lease backed by corporate.

I have passed on some good cash flow but it was because the properties were in bad areas or really bad condition and therefore would make an exit strategy a lot more difficult. 

They gave loans to people who couldn't possibly repay those loans, especially when their adjustable rate mortgages increased. 

Although I do plan to sell within the next 3 years (military orders) I want to make sure I didn't make a terrible mistake by lowering my payments now just to save a few hundred dollars but increasing my total loan.

I don't focus on residential or TK but when looking at those properties and areas look at various companies  and compare and contrast risk versus benefit.In those bad areas to find a good property manager you might have to pay 10 to 12% or more management fee as the tenant is more intensive and more difficult to protect the income stream.

Downside is split single contract into two, double closing costs and increased mortgage insurance costs.MY QUESTION:Does this sound correct, or is the underwriter mistaken...Do multiple townhomes require their own individual loans for each single unit (even if apart of the same structure)?

but a lot goes into analyzing a deal, including: $/SF, Average Days on Market in the area, how easy or difficult it is to get permits in the area, how long the flip would take, comps/ARV, Rehab, Rental Rates, how the area is trending, holding/carrying/hard money costs, closing/commission costs etc.If you can analyze the deal, you can then negotiate the deal with sellers, buyers, and lenders.

The property needs about  $400k in repairs to increase the ARV to 1.5 mill - 1.7 mill.