For some, the potential growth and lack of state income tax might still outweigh the challenges, while for others, the high property taxes are a dealbreaker.

Sometimes I question whether there is some real estate investor challenge I am unaware of where investors actively try to one up one another with new ways to toss their money down the drain. 

The biggest challenge, more than handling maintenance, is managing tenant relationships and understanding the legal responsibilities.

This is particularly important as you acquire more properties.Transferring the Property: If you're thinking about transferring your current rental property into an LLC, be aware of potential challenges that I have personally seenMortgage Implications: Check your mortgage agreement for any clauses related to property transfer.

It just goes to show that challenging yourself and pushing the boundaries pays off big time.

Compared to other parts of the country, in my opinion it's definitely more challenging to find good deals here based on everything you mentioned. 

In 2020, we took on one of our most challenging deals in Hudson, NH, where a woman reached out, desperate to sell her home and escape a troubled marriage.

I finally decided to close the doors mainly because the unit used was not available anymore, but also because the regulations got stricker and stricker over time.Now, if you want to use your 2-4 as an STR, you need to show proof that you are living in the unit you are renting by sharing a government-issued ID with that exact unit or your tax exemption form.If you have a building over 5 units, it's a bit easier but still challenging ( you can rent up to 25% of the units out for airbnb)...the few people I know that are successful are NOT the owners of the building, but more so the operator of the airbnb unit aka str arbitrage

There are two reasons DST portfolios have avoided some of the challenges seen in other syndications: DSTs usually have 10-year fixed financing, so debt costs stay constant and sponsors are not forced to sell for another 5-6 years minimum.

Expanding density is challenging to pass, but it can effectively increase supply and balance out costs.