Took a heavy wooden rocking chair down by the grill and left it there.

For example, we have not yet gone through an eviction or experienced the consequences of an unscrupulous vendor (although admittedly our PM and contractor aren't my favorite vendors ever); would y'all typically advise that we wait around for some of these experiences to rack up first before swimming in deeper water?

That first leap of faith into real estate sure is nerve racking but a blessing nonetheless.

When looking at beach properties I purposely purchased a mid range property as opposed to high end which are amazing and deliver higher income but tend to sit on the market longer, racking up more holding costs, than less expensive properties. 

Debt does sound scary but keep in mind you are buying assets not racking up consumer debt.

You must be racking up like million points!

Nests are typically marked off with 4 wooden stakes and have plastic / caution tape wrapped around the posts.  

Here’s what savvy investors are doing now:Closing Before the Finish LineDeals that close by October should give investors time to rack up management hours and qualify for 2025.

It's like a cell that is expanding but the core is decaying.Just thinking about these homes built in the 30's - 40's - 50's with cast iron pipes, wooden frames, and inefficient electrical systems, what other options are there to keep these areas from falling apart?

As a bonus it will cash flow better in this configuration, it's just harder to dispose of in future if I ever decide to sell.My initial plan and desire was a duplex, though the floorplan of this particular home doesn't lend well to being a duplex given that it's bifurcated by two heritage-protected wooden staircases, with each split in a duplex (either side-by-side or top-and-bottom) having a somewhat linear flow that would require multiple room subdivisions/new hallways to allow for rooms that can be categorized as bedrooms; though it does work as a SFH, triplex split 2/1, quad split either 2/2 or 1/2/1, or five-unit 2/2/1 with the addition of just three new partition walls, the sealing of several doorways, and the removal of a partition wall put in by the last owner to subdivide a kitchen based on a floorplan that no matter what I just can't wrap my head around.