I have dabbled in various types of real estate investments, ranging from small multi-unit properties to single-family homes and commercial buildings.

I'm looking to build a 200k guesthouse in my backyard that will have good cashflow.

That could mean working with an investor willing to fund the deal for a share of the profits or starting smaller with a house hack or live-in flip to build credibility, or putting sweat equity into a deal with a partner to learn and build your track record.

These can help you build capital while gaining valuable experience.

A lot of buildings don't have a carrier willing to insure at all.

@Jason Weidmannit's only solid if:1) you pick a market that you can go to in person and build a team first, and 2) you recognize that RE is a long-term investment, and you may have to wait 5-10 years, or longer, before seeing ANY return. 

If appreciation is part of your long-term wealth-building strategy, holding onto this asset could be wise.That said, if your main goal is to aggressively pay down your primary residence mortgage, selling could make sense.

.✅ Reduces Stress & Burnout – Investing should be about building wealth AND freedom.

@Ella Marie the Pro's are you can build long term wealth, the Cons are you can lose money if you cannot properly quantify risk.

Your build backwards approach totally makes sense.