I don't think enough people consider this aspect.Selling Stock: Selling part of your portfolio could work, but the 15% capital gains tax might make this an expensive choice unless the stock has underperformed or you’re diversifying away from riskier investments.HELOC: Using a HELOC on an existing property is a flexible and relatively low-cost option.

A weak team leads to guest complaints, maintenance issues, and poor reviews.

I don't see it as an issue but many still do, at least in my small town where the majority of renters are elderly people looking for low maintenance housing options.

None of these communities will be changing to residential neighborhoods, although a couple do have residential 'sides' that full time residents live in and can not be rented short term.Two of the big communities that you will have some issues with self managing are Reunion and Margaritaville.

Funny thing - I was with Compass until relatively recently (March/April 2024) as well.

Relatively small amounts of interest income ($1600+ per year) is the highest taxed form of income I have found if you have kids at home.After earning a few grand in interest, It takes away my child tax credits and gives me an effective tax rate of 70%.   

@Bryan HartlenManaging low-end properties can be demanding due to higher tenant turnover, increased maintenance needs, and frequent rent collection issues.

Quote from @Jim Stanley: You should reserve insurance for large claims.Contact the city and report the issue to them.

The buyers did a long inspection, multiple days... made a huge request for concessions based on what we knew to be purely made-up issues.

The best way to connect and learn is to be in rooms where it's going down.In terms of captial your best bet is to focus on a primary income that cash flow sufficiently, saving as much as you can and doing something real estate related so you can get familiar with the industry.