Not enough current income to move the needle, but all the knowledge required to learn and, if you're self-managing, the always-present "the tenant could move/break/have problem any minute of the day" possibility. 

It can be complicated at times, but breaking the overall process down in to smaller pieces and taking them on one at time definitely simplifies the process.

Problem with many of them I see this far north is November thru March they kinda sit or you have to discount the daily rate so much that you only might break even.

There was no evidence of breaking and entering.  

I’ve heard from some investors that are perfectly okay with simply breaking even on rental properties in the current market, but I’ve never had the risk tolerance for that.

Start small, maybe with a property that needs lighter rehab, and view it as a learning experience rather than a make-or-break deal.

Break down your rehab into individual jobs, for example get a electrician for electrical work, a plumber to repipe the house, a dry wall guy to close out the walls, etc.

The additional income from STR could justify the renovation costs, but it requires active management and market awareness.LTR or Break-Even Strategy: Renting long-term might simplify things, but if it only breaks even, you’re right to consider if appreciation is enough motivation to hold.DIY Basement: DIYing the basement could increase STR appeal without the full $50K outlay, especially if extra space attracts more bookings.

@Ori SklootGreat post Ori, thank for breaking this down.

Also from what I've read online breaking into the insurance side of things sounds like it requires cold calling and building relationships with those reps vs just registering property in database and waiting.