Math tells me I should be able to find a hard money lender to leverage my net worth in exchange for a run at all these assets but i'm somewhat curious if that line of thinking is too aggressive and borderline reckless.

A vocal minority have felt rates are JUST DESTINED to go outta control any time now from RECKLESS?  

You could allow applicants to enter without supervision and this would be fine until you have that one person that causes a problem, like squatting, and then you will realise how reckless a decision it is to allow a stranger into a property worth tens or hundreds of thousands of dollars unsupervised.The reality is that if a owner does not want to do the work or is not interested in doing the work associated with operating their business it would be wise to either hire a responsible property management company or sell.As some have indicated there are simple and cost effective ways to do it but safe is not possible.

Lending here was completely reckless prior to the crash.

I know investors who are far more reckless than me and they do everything willy nilly.

@Chad Duval As Thomas S. said, your contracts are of limited term and therefore can be changed very easily (i.e. basically every month) as long as you notify the tenant of the change as per timeframe described in the lease (and/or local laws, whichever applies).As regards your statement of "making money" on those pets:  while I get the idea, you probably won't make any due to the additional wear and tear, if not even damages caused by the animals (as a broad and general statement; I personally know no cat that would ever pee on the carpet unless their owners are reckless idiots and don't properly provide for them).

It wasn’t until I was 30 that I mustered the courage to try to follow my own path.My progress:Year 0: I'm not as reckless as my intro may imply...

If you add utilities into their rent, make sure you give yourself a little cushion cause some tenants are reckless with utilities when they aren't paying for them.6.

In either case, taking the time to learn the process before jumping in recklessly is much more likely to yield good results. 

Saying otherwise is reckless.