They then issued a special assessment where each owner got charged a percentage of the total bill that included the expensive sewer line replacement, but our portion was less than we would have paid to fix our own unit, so we were fine with that.

We stay in them several times a year.I'd say my biggest concern is assessments. 

Join the conversation to learn about the process of appealing your property tax assessment.

@Marc Shin, I echo Gino's thoughts.First the financial: assessing any improvements will come down to how those improvements affect both your cashflow and your overall value of the asset.  

(a) Anyone entitled and desiring to redeem real estate under the provisions of this article must also pay or tender to the purchaser or his or her transferee the purchase price paid at the sale, with interest at the rate allowed to be charged on money judgments as set forth in Section 8-8-10 (as it is now or hereinafter may be amended), and all other lawful charges, also with interest as aforesaid; lawful charges are the following:(1) Permanent improvements as prescribed herein.(2) Taxes paid or assessed.(3) All insurance premiums paid or owed by the purchaser.(4) Any other valid lien or encumbrance paid or owned by such purchaser or his or her transferee or if the redeeming party is a judgment creditor or junior mortgagee or any transferee thereof, then all recorded judgments, recorded mortgages and recorded liens having a higher priority in existence at the time of sale which are revived under Section 6-5-248(c).If the redemption is made from a person who at the time of redemption owned the debt for which the property was sold, the redemptioner must also pay any balance due on the debt, with interest as aforesaid thereon to date.(5) Mortgagees of the purchaser, or their transferees, are considered transferees of the purchaser, and a party redeeming must pay all mortgages made by the purchaser or his or her transferee on the land to the extent of the purchase price.If the purchaser's mortgages do not exceed the amount of the purchase price, the balance must be paid to the purchaser.

So far, Marketplace and Email blasts have yielded the best results.

Personally, I don't like condos- HOAs and surprise special assessments can eat up any potential profits and in most states, they can just change the rules when they want to and decide that LTRs or STRs are no longer allowed. 

If you are not comfortable asking other successful hosts who they use, you might want to look for a group on Facebook marketplace for your market and look for newer cleaner/handyman that are starting out and hungry for business and to do a good job.2.

My houston properties are getting re-assessed for new HOIs, I am looking at Hawaii and finding it hard.

Recently submitting an appeal for my house, I was told that there is a rick that an appeal could lead to a higher assessment if it's found your is undervalued; typically uncommon in Cook County. https://taxbacknow.com/