I do well, at least enough to go on vacations as a family, put money into high yield savings accounts, max out the ROTHs and add to investments when I can with money saved in savings and checking accounts.

Another idea I would recommend especially as a business owner or investor would be to consider going to a BNI or Networking in Action type of meeting as a guest.

@Nathan Johnson "Our savings are minimal, since teaching isn't very lucrative and life is expensive."

I would keep the brokerage account and focus on the tried-and-true practice of saving up for a new investment.

One idea might be to offer a discount or incentive for extended weekday stays—say, booking three or more nights—to encourage longer reservations.

They said they'd accept a 6 month term instead, but they're not being very forthcoming about what their sales record has been (I asked for the last 12 months just to get an idea, but they ignored the question :( ) and I'm getting a not-so-great feeling about working with them....The home is 2-stories, attached garage, 4bd 3ba, 2269 sqft and sits on a corner lot with a huge backyard (lot is approx .13 acres or 5662.8 sqft).

Don't start throwing ideas at them like seller financing or numbers etc until you have an idea of if they actually intend to sell and what their needs are around the sale.

You could convert them to a DSCR loan but then transfer them to a LLCWhat we have done is save for down payments and renovation costs, - buy properties that need work rehab them and then refinance them out making sure it meets our dti.

I’ll break down my thoughts on your current strategy and then toss in an alternative idea for you to chew on, since you’re open to almost anything.Your Current Plan: You’re in a strong position with that $1.4M paid-off student rental and the second one carrying the mortgage and living costs—that’s a fantastic cash flow engine.

In that process, I got my real estate license to buy the house and save on fees.