So I started trying to get creative on how to create a win-win-win for all.Here’s how it went down:I got the sellers to agree to an asking price of $180k, a full $40k over what they originally wanted.In the offer, we included a seller credit of $34k.This strategy allowed me to cover the extra commission for both the buying and selling agents and ensure the seller got exactly the cash they wanted should they have sold it at 140k.With the seller credit, this reduced my total out-of-pocket expense to just $6k.I used a commercial DSCR loan product with a local bank.

Expect to be asked to write a letter attesting to the fact that you value a short commute over the extra bedroom, maybe WFH is over and you have to start going to the office again, the 4th bedroom was your home office, but you no longer need it... that certainly makes sense and would also go through with any lender that ever wanted to get my brokered business again. 

It became too difficult to trust that the extra work being performed was actually needed.So, I decided to take matters into my own hands.

Another thing she told me was that she would like to stay an extra 30 days after the closing date, meaning that she would like to move out on the 28th of July.

Must have a smoke detector in bedroom.If you're not on town sewer is the septic design capable of handling the "extra" bedroom? 

I will assume his loan and he pays me his mortgage, plus a little extra.

A trust may offer some of the same benefits as an LLC, depending on your goals, and allowing you to claim the part of the house you live in as homesteaded tax.Make sure you have the right home insurance and consider an umbrella policy for extra protection.Certainly buying a house, using conventional financing with limited money down as a primary residence and renting out parts of the house to help pay the mortgage, is a smart financial move.

House hacking it for a year or so, could allow you to build up extra funds for a future down payment, furnishings, and other costs. 

On the flip side, I could room in an apartment with a roommate for $900-1000 and save the extra cash for a year to put into another property.

If you plan to pay down quickly, splitting into two loans makes more sense because you can attack the more expensive loan with the extra principal payments and rapidly change the weightings, reducing the blended rate with each payment (fyi - most investment property 2nd liens will have prepay penalties).