Hi experts,There is a property I'd like to purchase (for sentimental reasons) to live in in about ~5-8 years.

Regardless of whether or not having a short term rental in your small complex could help or hurt property values and your ability to convince the HOA of the former, please think about the viability of your STR if the neighborhood sentiment is anti-STR.

May I add to the sentiments of  buy right and manage right. 70% of my holdings are in Price Hill.

@Maxwell Ventura sentiment matches my views but I wanted to clarify.  

Quote from @Anthony Freeman: You can be one with W-2 income as long as you document and dedicate the mandated hours@Anthony Freeman That a very nice sentiment, but having to document working two full time jobs? 

I share the same mixed sentiment. 

@Adam Regos, there is some great advice in here, and I originally came in to echo the "don't try to time the market" sentiment.  

@ Patricia Steiner, my sentiment exactly ...no discussion needed-Just say no

But given the past performance and reviews (and general Vacasa sentiment here and other forums) of the unit I'm not leaning towards continuing using Vacasa.

I think I agree now with the sentiment that it’s better to use insured contractors on high risk jobs, and okay to use uninsured for low risk jobs.