It's impossible to answer your question without knowing how much you have to spend to acquire the house.

We plan to remove them all to protect from tax increases on our current primary, but I am afraid that now that the other properties won't have homesteads, we may see skyrocketing tax bills and it will eat into already small cash flow from rental income.Does anyone have advice for how to handle this situation other than just increasing rent?

I am glad that I am not the only one who takes twice as long and spends twice as much, haha.

Had to spend additional money to get everything fixed.  

They care about making money and protecting their asset.

That protects you from having to sell to  low.

@Tar-U-Way Bright Using your LLC for real estate ventures offers legal protection and tax benefits.

If not they could spend money and time and offend buyers if they update the property incorrectly.There are other options, such as landlording.

You said "don't do it for the money," but I'm sure money calculations were part of convincing you this would be a reasonable way to spend your time and money.

Here are the numbers:$30k - avg monthly income3 options for rent vs buying$12.5k - avg monthly payment (20% down) on $2mil home$6.25k - avg monthly rent on $2mil home$6.25k - avg monthly payment (71.5% down) on $2mil home3 options for return on capital:7% - avg yearly return on 71.5% down payment (assuming 5% avg yearly appreciation in SD)10% - avg yearly return on from S&P 500>10% - avg yearly return on investment property (just an assumption, but I think you are all here because you beat the stock market)First, the $12.5k monthly is very intimidating and beyond what I should be spending on shelter (a no-go for me)