While your lease may indicate that the tenant pays, the biggest problem with this is that tenants will stop reporting issues for fear of paying.

The biggest difference to me is that YOU have control of every aspect of an active investment, while somebody else is in “control” of a passive investment.  

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

I think your biggest issue with any "work-arounds" is going to be your legal liability and holding the proper insurance in case something goes wrong, which I'm going to assume you'd need to be properly licensed in order to be properly covered by insurance.

HOA fees, in particular, seem to be the biggest hurdle.

The biggest challenge was addressing unforeseen structural issues, which ate into the budget.

The biggest challenge was addressing unforeseen structural issues, which ate into the budget.

I put the odds at 97% an investor does very well, 2% that through no fault of Praxis' the housing market and/or the economy enter a tail-spin due to inept political leadership at the highest levels, and 1% that Brian is the biggest fraud ever to fool me. 

The downside, if trying to maximize the profits, is that it can take months to solve zoning and land use issues which is required to sell at a retail value.  

The biggest thing to make sure of is to choose a solid strategy that you plan on using for the long term and choose a city/state that you trust.