(I changed my trip to Indiana this month so I could attend a multi-family meet up in Indianapolis.)

well there are certainly no shortages of houses or properties to buy in those markets.. one 3 day trip and you would spend all your money easy... although most of the sellers want to sell turn key to maximize their profit.. and if your trying to remote rehab your taking on a HUGE risk that you need to be very cautious of

I (reluctantly) stay in them now that we have a kid and want to do family trips with the grandparents and other family.

Still trying to find out if I can write this trip off.  

I have been searching property listing for several months, but have just determined that I need to do a scouting trip to the area.

You may want to look for wording to indemnify clauses and keeping your business / or self safe for trips, falls, accidents on the property. https://my.mnbar.org/residenti...

I needed to check myself before making the road trip.

To all my Milwaukee members…I’m making a quick trip to Milwaukee to check out the area for a future multi-family investment.

Multiple trips through the summer.  

Correct, the issue isn't about HOA, they aren't very strict about this, the issue is with power tripping from the cop that moved recently and thinks he can act like a judge.