I'll keep my short and sweet, I've always had a PM do the majority of my day to day and clean-ups, but at the end of the month I get billed and for each hour and they have a category with a quick explanation. 

There's even a person who started a crime scene cleanup business and also offers to buy the disaster properties from her clients vs cleaning them. 

In addition to periodic cleanup and taxes, you probably want the IRA to have some kind of basic liability coverage in case someone goes on your land and does something dumb.Depending on how many lots you intend to purchase, you will want to weigh the option of a checkbook IRA LLC or Solo 401(k). 

Add on that your history of poor money management and you have a recipe for a repeat performance of wrecking your credit.Get some professional help with money management and clean up your credit and get some savings.

I purchased a distress 80 unit complex and after working on it and depleting all my funds I have been left with $285,925.24 of uncollected rents/damages created by tenants I have evicted or have broken the lease from April 2007 to present.

If I paid it, I'd deplete most of my savings.

Getting the lowest balance out of the way is usually the quickest way to start snowballing extra payments into other debts you want to clean up. 

Clean up repeat and outdated listings.

Just a helluva mess to clean up.

Of course, you will be buying vacant properties that may need a little clean up so you may be paying for a couple of months of mortgage payments, utilities, insurance, HOA fees, etc with no income on the property yet.It really depends on your specific situation, but I recommend either working with at TK company or finding MLS assets similar to the ones listed above.