Proceeds from the disposition of an asset - say you sell a rental property in a few years - are considered capital gains are and taxed accordingly.Note:  If you flip properties then the properties are considered inventory, not capital assets of the business, and all proceeds are treated as income.

So proceed with extreme caution.

He's given me some pointers on how to proceed, however I'm not sold on his course due to the fact it's not my business model.

if the property is damaged by fire or other casualty loss and the cost of restoration does not exceed 1.5 percent of the purchase price, the seller must restore the property and closing shall proceed according to the terms of the contract.

Since I owned the home for 10 years, as I understood it, I didn't have to pay taxes on the proceeds so I didn't file any paperwork.

If the tenant does not voluntarily vacate prior to the hearing, you (or your PM) will go to court with your attorney and either mediate the situation to come to an agreed move out date or proceed with the hearing to ask the court for possession of the property back.  

You would bring a deal to them and split the sponsor's equity.Then and only then you should be able to proceed on your own.Hope that helpsNick

Continually funneling out your proceeds is counter to that goal.

I'm in the final stages of divorce and after touching up my current house I'm planning on selling and using the proceeds to house hack my way into rentals.  

So I will ask for it from the seller.I am however looking to buy a property from an individual, how should I proceed if I want to make sure we have a clear title?