April/may the bookings dried up.

You need all that because the day STR becomes illegal they’re going to walk leaving you high and dry. 

These old houses sometimes have sewer issues, and this place looks like Roots City International.To me the house looks "Cared About", I see some proper looking wood trim under the porch, the porch columns were not replaced with 4x4's, all windows match, etc...Plus this house might have an interesting set of interior upgrades such as built in shelves, etc...I say that because the front door looks like it has 2 side lights (a big upgrade in the olden days).And I suspect the stairway may have some elegance to it, such a a landing where that small window is.With all of the close in trees, the gutters may be full of leaves and you may find rotting wood at the edges of the eaves, and many of these old homes a have boards under the shingles vs plywood, so you only talking about replacing a board vs a big rectangle.Good Luck! 

With higher interest rates I can't see the demand staying high...combine that with some layoffs, people not working from home, credit increasing, savings decreasing, these retail investors taking a huge L in the stock market/crypto and the demand has got to dry up a good bit, or a lot bit in some "overpriced markets" - florida, smokies, austin, bay area etc. 

This is why most either fail, or never make as much profit as they could/should.A book on basic business accounting would be a good start......but those are so dry, and most contractors brains are wired differently, that's what makes them good at what they do.....

Roof leaks, leaking supply or waste pipes, tub surrounds, cabinet bases (between the interior bottom of cabinet and the floor), all can create these slow leaks that rot wood and can "feed" mold and attract other pests that could be causing your issues.You might also have a professional perform testing for mold.

Multi-family (5 or more units) doesn't make sense on top being competitive and dried up in most markets. 

There is no cut and dry rules.

No motive for monopoly, no motive to bleed people dry.

The rivers are dry in parts most of the time as water is stored behind manmade dams up in the mountains and released when the snow melt gives those reservoirs a surplus.