The real question is if you need to add a property management professional to your team, and when to do so.

I talked to the roof company and they said it is very complicated so I didn't.  

You can keep all your properties under one roof, so to speak.Cost Considerations: Keep in mind that setting up an LLC comes with some costs, like filing fees and compliance stuff.

Analysts predicted about 160k new jobs, so it's still slightly off compared to experts' best guesses.

So now on 1st September my property is vacated and needs some TLC but their broker wont show it to anyone till the work is completed. 

Few more points:Their lease is valid till May 2025.This is the first time she even told me about mold.In the email she did ask me to settle the lease.I have a little less than a month of rent as security deposit, which I am ready to settle without any additional penalties for abandoning the property.At this point I am okay with her leaving the place, just I want to get the control of the property back to fix the mold issue.History:1) Recently the AC has been replaced and after that there was some intermittent issue with the installation (temp doesn’t reach target intermittently) and I had to call the tech back 5 times to finally get it resolved.2) Also last month I replaced electric range with Brand new Electric range.3) Two months back she said the refrigerator was leaking, I asked her to send picture of the make and mode of the refrigerator, but I never got a reply back.4) Also for last 4-5 months she has been asking me to send her 5-day notice so that she can claim reimbursement, I was sharing a document and she was paying the rent a little late.

If so, is there a limit to how long we must hold the home as an investment property before we can move in and convert it to a primary?

The question I have is have any of you rented out a property with a pool and if so what safeguards should I have in place to protect my myself?

to have money to put into improving the property so that it can be evaluated higher?

So, that clearly implies that you have an income source that you are basing your budget on.