Hi @Eric Dekker, and welcome to Bigger Pockets! Congratulations on your first project, that is awesome news!
1. You definitely brought up some interesting points in your options list. If the first project went smooth for you and the financials worked out then maybe trying to replicate what you just previously did again with the new knowledge I am sure you learned from the first project might not be a bad idea.
2. Depending on what your current living situation is, I think this is always a great option for anyone. Especially if you currently rent and the rent is expensive doing this can help you save much quicker to continue investing while also potentially making you additional money on top of that.
3.I my self have been conflicted with short term rentals as well. You brought up a really great point, if times do get worse this really may make that sort of project much more difficult and throw off the numbers completely. Another thing I worry about is the dynamic of the rental services such as AirBNB. I do not know a ton about short term rentals but I always worried about what would happen if these major companies changed the rules in a way that would make it more difficult or potentially take a bigger cut. Again, truthfully I do not have that much experience with short term rentals so I could be speculating. This is just some things I think about when considering it myself.
4. Also another great point that I again am also considering currently. My view after investing for the past 5 years or so in 7 different properties so far is I always want to now put myself in a position that if a great opportunity does come up I can jump on it. So for me this means maintaining a certain amount of savings while now also having relationships with people who I can borrow money from or invest with if the opportunity does present itself. Another thing to consider with this point is something my mentor always says, unfortunately if the money is in the bank you are losing money anyway, at least if you invest it in a smart safe way with a property that cash flows you are still making money.
Personally in your situation I would make this decision based on your current living situation. If you are renting, than eliminating that overhead while potentially making money on top of that through buying and living in a multi family house seems like a great idea. If the rent is cheap or you currently live rent free, then you can still buy a multi family and that cash flow will be there.
You could also wait but as a lender myself interest rates rising at the same time the houses potentially decrease are still going to make the houses less affordable.
A lot to think about haha. Hope at least something I mentioned helped!
I sent you a request as well. I would love to connect further!