@Shiloh LundahlThey are tenants and not squatters however the remedy is the same......an eviction Obviously, that is not going to happen currently.

You need to be aware of the Residential Tenancies Act in the jurisdiction in which you are acquiring property.  

The repayment terms for a 401k participant loan are equal monthly/quarterly payments of principal and interest (typically prime plus 1%) over a 5 year term (longer if used to acquire your principal residence).Please note that if you take a full $50,000 and then pay back the loan, you can't take another $50,000 until 12 months after the first loan was fully paid back.Per the loan offset rules that went into effect with the 2018 Tax and Job Act: if you leave your job and the loan is current at the time you leave your job but then the loan goes into default because you left your job, you will have until your tax return deadline (including any timely filed extension) to make the loan current by depositing the outstanding balance into an IRA (and thereby avoid the taxes and penalties that would otherwise apply).Please keep in mind the multiple loan rules:Under those rules, the sum of the balances of a participant's outstanding 401k loans under a single 401k plan (using the highest outstanding balance of each loan over the last 12 months) can't exceed 50% or $50,000 whichever is less.

I am thinking that I can leverage one or both of my properties as collateral to acquire a loan for the 4 without a 25-25% down payment.

Purchase price: $305,000 Cash invested: $2,000With the proceeds from my first Live-In flip I was able to acquire this beautiful pre 1920's brick foursquare on a historic street in North End Hagerstown, MD.

I live in TN and acquired the first property through Roofstock and this latest deal found on Loopnet.

I live in TN and acquired the first property through Roofstock and this latest deal found on Loopnet.

I put the offer in on the duplex I bought because they had paperwork and an engineer report on file for what they did to remedy the issue. 

If I acquire a second house subsequently, rehab it, rent it out (past the "seasoning" period), and try to refi it to get some money out to repeat the process, will I run into issues with the mortgage on my first home when the lenders see that I do not have income from a job to pay for the first mortgage, thus will refuse refinance of the 2nd house?

Acquiring roommate this summer.