That way, I have my agent's opinion, an inspection report, and an itemized bid from my contractor.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

The best way to do this is develop a great working relationship with a real estate agent or escrow officer and they will provide you with reports for free. 

So we shopped it out to our consistent buyers but at a strong price of $75k.

We walked the house and clearly there was an addition added at some point.Is this an issue that the title report and MLS doesn't match? 

If we're consistently profitable and find that the cleaner is not effective in responding to guest needs, then we will not hesitate to go the dedicated on-island agent route.

You will have a heart attack when you get your first inspection report. 

In the case of a successful tort against you, you might regret commingling funds in a single bank account, but I can't see how keeping them consistently separated would ever burn you, even if it is a bit less convenient.  

So my inspection report came back and it cited the same egress requirements.

In order to negotiate the deal, I used the inspection report to help me get a better price.