I use Proper insurance, unwritten by Lloyds of London, for my STR - covers the extra issues you would expect from an STR like vandalism, alcohol liabilities, business interruption up $10k, hot-tub cooties etc.

Congrats and knock out that extra debt you accumulated so you can save up for STR #2!

There is usually extra charges on closing to pay for that service… but it is minimal.All the best!

Or sell using the 1031 exchange along with a partial 121 primary residence exemption There is a way you could take advantage of the 121 primary residence exclusion allowing you to take the first $250k of the gain tax free ($500k if married) and qualify for a 1031 exchange.Say you purchase a property as your primary residence (house hack extra rooms for extra income) and lived there for two years while stationed there.

In most cases, cash flow is already tight, and adding debt could put extra strain on your returns.

On my lot where I live, I can have as many kitchens as I want (not sure why I would have extras) and can build a tower, but they won’t let me build an ADU for my mom unless it is connected to the main house.  

You’ll need a real estate attorney experienced in creative financing.Land Trusts for Extra Protection – Many investors in Illinois use a land trust to hold title when doing subject-to deals.

(A little background) Our primary home has a balance of $327,000 at 2.9% interest While our investment home has a balance of $88,000 at 6.4% interest I plan on paying off both back to back by recycling whatever extra income I have, but was weighing the pros and cons of which to pay off first.

Hi Brian, I have Obie in my properties now, although I've never filed a claim with them so far, they are the better rates I can find, ask for their tenant liability coverage, I paid an extra 107 dollars a year and they cover up to 100k if a tenant severely damage your property. 

I expect renovations to cost $60-70k (I’m padding in extra for worst-case scenarios, I’m conservative like that).