How to know when is time to replace the roof. 

We need 1.8M to pay off the first mortgage, mechanics lien and finish the project.

I just feel like the equity portion is a nice asset to have and not have to use all that cash.

Currently shopping around for a convention loan for first home to house hack.

After the current tenants move out, I need to replace the carpet and pad. 

I am wrapping up my licensing education with the intent of being able to buy and wholesale solo part-time, while keeping my full time job.How would I go about finding a brokerage that would sponsor me as a sales agent while allowing me to have this flexibility?

You don't need to qualify for REPS to use the STR loophole.

Elena-  You may also wish to visit NARPM.org. 

I'd advise you to pick a service that partners with the Campaign Registry to let you register a phone number in order to comply with TCPA and benefit from optimal deliverability.

But I suspect you will find what most do that its darn tough to next to impossible to pull off.