If you're at a loss and paying off the shortage still puts you at a loss I think your best bet is selling, or seeing how you can get more income from current rents by making it mid term/seasonal or an air bnb. 

Hi Hannah, CPAs can provide ongoing support and guidance throughout the year, not just during tax season.

If you are using battery powered you have to change codes often (one code for showing - should be deleted after showing season, one code for tenant that needs to be changed after each tenant) and you need to replace the batteries every time it goes vacant so that you don't end up with a tenant dead battery and a tenant locked out.

Would love to get seasoned investors' advice on how they would solve this investment/tax challenge: I am about to transfer 300k from a retirement vehicle so that I can use the money to retire early.

In the Mountain market it is property dependant and seasonal dependant.

There are players that you may want to deal with in the future that may be concerned that you would slander them from the rooftops over the slightest of offensives. 

Then tell the agent to run comps for ARV based on updates you do.And you also said you can't afford to lose $20-30k, the most seasoned flippers/investors lose money all the time, and ultimately that is part of your education costs, hopefully you don't make any costly mistakes, but you have to run your numbers well enough to make sure there is some 'ooops' fund to help shield you from that.As for comps, typically, appraisers want them to be in the same neighborhood, within 15% same square footage, same # beds/baths and age.

Whether you're looking to dip your toes into the real estate market as a house-hacker or you're a seasoned investor seeking your next big venture, I'm here to guide you every step of the way.But that's not all.

I live near Chicago, so we get all 4 seasons and a ton of moisture. 

The number of pending listings has been going up since January which is normal not that we are in the spring buying season.