I filed claims on those properties after the reforms, but the insurance companies stood firm this time.

It was simple and cheap.However, it still takes time and money to set up and maintain the LLCs.

For your first question about doing a "subject to" on a hard money loan, it’s possible, but it’s not as common since hard money lenders typically have stricter terms and might not allow a loan to be assumed like a traditional mortgage. 

Investment Info:

Single-family residence fix & flip investment.

Purchase price: $95,000

Cash invested: $25,000

House went to tax lien auction, homeowner was going to be homeless with no money. We...

My question is, when is it the right time to start using a property management software and which one would work best for my current situation.

This could be structured as either a lump sum upfront or monthly payments over time.

It all comes down to timing.

@Stuart Udis, when I first started reading your post, I thought you were being serious.  

That way, you'll have plenty of time to tackle any problems head-on.

I am under a time crunch and would like to purchase the property asap (due to tax reasons).