I don't think your first property needs to be perfect, but doing the work in advance gives you the possibility of refi (in a good rate environment) or more equity on a HELOC.

It's more "here's what we've got, it's peaceful and pretty, come pay nightly to enjoy it up to 29 nights".

But the 199A is scheduled to sunset in 2025 under the TCJA unless made permanent.It wouldn't be uncommon for some investors to only realize taxable income on 40-50% of their dividend distributions in today's current environment (I have seen this personally).You asked about fees, so one quick comment.

However, I believe it has deflated a bit recently due to the current interest rate environment, increased inventory of nearby new homes at a low(ish) price point, and the neighborhood turning to mostly investor owned homes.I do have mortgages; the tenants are paying these down. 

My properties are primarily in Arvada, CO, but I have a pulse on the market of regulatory environments throughout the state since I am almost entirely niched to STR investors in my business.

While it’s a bigger initial expense, it aligns well with your long-term retirement strategy and could provide peace of mind for years to come.

Sponsor is realistic about current market conditions, and is humbling themselves on current portfolio, while also realistically appraising current environment as a potentially better buying opportunity than the peak 3 years ago. - Sponsor learns from mistakes.

The larger unit will have higher maintenance/cap ex even with coastal environments being harsh on some items.I suspect your expense estimates are far too low especially if you kept the BP calculator default percentages.  

It could give you peace of mind as you focus on your family and move to your new home, without the additional stress of managing a second property from afar.Best of luck with your decision! 

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