This is pushing many to look at areas that still offer strong cash flow backed by solid economic factors.I’m originally from Florida, but experienced the same issue after factoring in all the expenses.

I'm actively working through this process somewhat now so I can roll funds into a bigger boutique hotel project.

In some places, from what I read in Forbes, even a finished outbuilding might be noted separately rather than rolled into the main house’s footprint.

.: It sounds like you have a great system down, and I am sure that you can find some handymen that are in the area doing part-time work and then working at a day job that could be pushed into full-time work on your properties.

Ensure the rents and expenses support the debt service and provide solid cash flow after covering the assumable loan, seller carry payments, and operating costs.Occupancy & Rent Roll: What’s the current occupancy rate?

New listing typically get artificially pushed to the top for a short period of time.

Out of bed before 5 am - (I had a separate habitat for starting the day right but then slowly started pushing my time of getting up back2. 

As mentioned elsewhere, breakeven on cash flow is not the same as break even for taxes.Let's make some assumptions:Rental income = $1000Mortgage payment = $400 - but $300 is interest and $100 is principalOther expenses (repairs, advertising, utilities, etc) = $600Depreciation = $250The above scenario creates a break even from a cash flow perspective, however the tax scenario looks like this:Rental income minus the mortgage interest (principal is not deductible) minus the other expenses minus depreciation looks like this:1000-300-600-250 = $150 LossIf your income is over $150,000, then you cannot deduct that loss, but you can roll it over to future years. 

Most really successful people keep pushing forward because they are either competitive/driven.  

Getting it under market value would be a bonus.So, would using an FHA 203k renovation loan, which would allow me to buy something unqualified for a standard mortgage, which would weed out a lot of competition and push the price lower.