This may be a long post, but I thought it would be good to walk through everything step-by-step, and explain my thinking along the way.If you want to stick with me through it all, here we go:I was not going to be getting a conventional mortgage for my first property for a number of reasons.First, I am still annoyed at the hoops I had to jump through to get a mortgage for my primary residence.Second, my liquid cash was on the lower end.Third, the properties that I would need to start out with would not be financeable anyway.Fourth, my DTI is on the high side, due to the decision that we made to take out a HELOC to complete interior improvements on my primary house.So, I decided that my path was going to be to form a single member LLC, and take a loan from my 401(k) at work to finance the down payment.Since I do not view the 401(k) loan as a long-term solution, I am treating like hard money, and pay it off ASAP.So, my first deal would be a flip, or a rental that was such a good deal, that I could re-fi out and pull all my cash out.I decided to reach out to the commercial lending department of the local credit union, which I am a member.The person I talked to (who became my lender) is fantastic.I told him what types of properties I was looking for, and that I’d look to turn them into rentals, or to flip them.I will never forget his response, which reminded me why I love this credit union.He said:“Typically, the deals you are talking about are much smaller than the deals we like to do.However, we also realize that you can not get to that level unless someone helps you get there.So, if the numbers make sense, we will see if any of our products fit.”Awesome!

The idea that a vacant house has enough equity in it for you (or in your case an investor) to purchase it, paying off the mortgage/mortgages and any an all liens and still have sufficient equity in it makes no sense.  

Some potential drawbacks to keep in mind are:Additional closing and loan origination costs (two transactions/mortgages instead of one) - speak to your lender and title company about costsTwo insurance policies instead of one - probably close to double the insurance cost as compared to a duplex - get a quote from a good insurance agent and compareTwo sets of property taxes instead of oneThese certainly aren't deal killers, and the benefits noted above may outweigh the disadvantages.

This is okay if you're doing just one and need cash in short term, but keep in mind you won't be getting mortgage prices. 

Over the months, we got close to doing a cash for keys on two separate properties, however one of them had a second mortgage that was a deal-breaker (which I should've saw before deciding to market to them).  

I'm really pumped to have this play out the way it did, and learned from it.I'm considering forgetting my conventional mortgage and getting a commercial mortgage and purchasing a multi unit property instead of a condo.

Starting earlier means that you start the mortgage pay down sooner if you Buy and Hold and therefore your properties are paid off faster as you get older.2.

I still work in education, the salary helps me out qualifying for mortgages and I can save all of my cash flow and build up my reserves.

I see guys quote for loans sometimes in the mortgage space 4% but it is NOT a locked rate.

In my opinion it is cheaper for you to list your properties through a broker that offers Flat Fee MLS listings services.