Yes, there is a chance the payment could be rejected for non-sufficient funds on the 19th, but I'm managing 400 rentals and it's pretty rare and the Tenants make good on it 99.9% of the time.

Your primary insurance policy with $300,000 in liability coverage should be sufficient in 99.999% of all lawsuits.5.

Being that you already have property management experience and feel confident in your ability to manage a single-family or multifamily property, it really comes down to your financial position.If you have a good amount of cash available to put a down payment towards the purchase of a property and maintain sufficient cash reserves (or if you have a partner you can work with who does), then there's nothing wrong starting off with a multifamily property. 

And my feeling is for MOST people Solo 401k is sufficient to meet their needs, and an actuary creating a custom plan is “overkill”.  

You act like you're doing the society good, you're BP's token Karen.

I think if you can write a solid letter of explanation stating that you are going to commute to Colorado from Washington for 4-5 months out of the year for your job (and why), that should be sufficient enough to run this as a primary residence. 

I hope you have verified that there will be sufficient equity and that you'll be able to qualify (either DSCR or Conv) for a takeout loan or cashout refi for the hard money.

While a detailed log is often sufficient, adding additional documentation can strengthen your record. 

But, something to add that you have to understand is that a 3-4 unit has to be meet the FHA self sufficiency test.

I need to ensure that the rent-to price ratio will sufficiently cash flow as I intend to hold at least 5-years before acquiring any other real estate.