We probably could have negotiated more efficiently to reduce the purchase price based on some deferred maintenance.

Have you changed you routine?

As a side note, is a pool something that can help a property cash flow better, or does the cost of maintenance offset or take away profit?

I usually budget 5% for CAPEX and 10% for Repairs and Maintenance.

Investor entry into these areas is low, but if I can’t get maintenance people to work on the property because of the neighborhood it’s not worth it.  

Then take him out for lunch and after, put a contract in front of him that spells out your maintenance responsibilities (labour and financial).

You still have several options, depending on if you want to invest directly in individual properties or be a bit more removed:Full-service turnkey investment: Should be mostly passive after you do your due diligence and pick a provider, but don't skimp on your homeworkYou choose which props to purchase, but have no control over tenanting choices, some say in large maintenance expensesAvg cost for solid B/B+ prop in Birmingham (and some other markets but this is the one I have data for, since it's my market) is about $100k per door; you'll pay market price for a tenant-ready, fully rehabbed propertyPartnering with someone who does the on-the-ground stuff while you provide capitalCan be passive if your partner really knows their stuff, but more likely you'd be fairly involved with the choices madeMore control since you call the shots with your partnerYou can pick which markets and price points you're interested inPotential for higher returns (ie buying distressed and then forcing equity through renovation) if your partner is experienced and can execute consistentlyInvesting in a syndicateMany investors pool funds to invest in much bigger projects like commercial space or large MFRs, or in larger portfoliosVery passive, investors are not responsible for project vetting or management, but you have no controlMay have higher bar for entry, some syndicates require large investments and you'll need to have liquid cash on handBuying shares in a REITLike an ETF but comprised of real estate investmentsVery passive, but no control over which assets are held in the fundHighly liquid, easy to buy and trade, lower bar for entryEverything is a trade-off between passivity and control, time and money.

We have seen that it takes finding about 200 properties like that (vacant, or occupied and needs maintenance) and sending mail to them 3x each to get 1 deal!

There's only around $150 additional a month for trailer rent over base lot rent, and I think that would be swallowed by maintenance costs quickly.  

It gives you a place to live, it lets you experience the buying process, the renting process, the maintenance issues, and depending upon how much work it needs it would let you experience the flipping aspect of things.