If you are just getting started in multifamily real estate investing (perhaps making the jump from SFR – single family rentals – or flipping) – make sure you are well prepared if you jump “up the ladder” too quickly – the world of 2-10 unit multifamily investing can offer a great “bridge” between SFR and Multifamily for any budding real estate investor.

Hmmm, guess you didn't notice that @Michael Plaks is an "Enrolled Agent".There are hot dog vendors, there are fast food cooks, there are sit down resaurant cooks and there are fine dining chefs. 

This could help prospective investors plan better for seasonal challenges and ensure they are prepared for higher maintenance during harsh weather conditions.For those interested in similar investments, your case underscores the importance of patience, unique property insights, the right financing, and effective property management.

However, given our current state I'm preparing to set-up my own website and/or post on various channels that don't appear to offer the host insurance and I know asking the Guest for security deposit or to run background checks can be a deterrent for short stays.

You may want to consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year, not just when preparing your tax return.

Your property management company will at least have the expenses of creating the company (I would strongly recommend creating an entity), bookkeeping, tax preparation and the 401k plan setup and management fees.

These aren't that hard, and I guarantee that the closing attorney who prepares your deed will be able to prepare these as well, or send you to someone who can.

To effectively plan your investment approach, it is important to educate yourself and prepare financially by attending seminars and webinars.

I'd sell it especially as it has a large lot and a pool (while some tenants love the space and pool, many are not prepared to take care of it). 

Just food for thought