I personally think it's worth it.

Research comps in the Milwaukee area or connect with a local appraiser to estimate your property’s potential value.Depending on the rental income, you might explore DSCR loans for your refinance, as they rely on property performance more than personal income.

No need for a PMS with only one.AirBNB and VRBO can handle things for you.In the end you won't save much time with only one STR.Plus, personal correspondence really works well to boost those 5 star ratings. 

I have personally stayed in one of these places where the main house is separated, and only the basement space which has a walkout entrance, its own kitchen, and two bathrooms would be rented out an Airbnb.

Do you have any personal experience with these types of programs?

Luckily, due to the number of items this person had at the home, we added charges for each day beyond the set closing date for them to vacate the property.

Both land investing and multifamily are great but what's best for you is more important.Land has no cashflow and is speculating imo too so personally it doesn't fit my investment thesis of buying property that produces cashflow.

This will allow you separate business income and expenses from personal income and expenses.Since you plan to house hack your bookkeeping and tax return preparation will be more complicated because a percentage of your home expenses will be personal deductions and some will be business deductions.

All lights were green and there was a pileup, leaving behind a mess of twisted metal and broken glass, and a few personal injuries to boot.The syndicator crowd coined the phrase "survive until '25" under the hope that by 2025 interest rates would correct and their deals would be fine. 

I also use Hubspot for my personal projects but really like Pipedrive as a paid CRM.