The IRS will consider extensive repairs as components of an improvement project.In my opinion, filling in the pool is a major landscaping improvement not a repair

If you need major tax deductions to offset other income talk to your CPA about component or cost segregation depreciation.

Are there more accurate ways to perform a comp on a particular property.

In the market today you cant simply buy right, the value add component needs to be sizable and in many cases is hidden from the trained eye. 

I plan on using my military connections in Tampa to get into the market for working with all the active and reserve component servicemembers in the greater Tampa area.

And frankly, knowledge is only one piece of the "puzzle", the main component is rather the personality - endurance threshold, confidence level, risk tolerance, common sense, persistence and resilience.  

Within every bubble is the greed component unfortunately!  

It gives me a good picture of the cash-flow in the most recent fiscal period (typically a year), but to carry that forward 2, 3, 5 or 10 years encompasses as many assumptions and predictions as does calculating an internal rate of return.Now, you can discount future cash flows and endeavour to calculate a series of CoC values ... or, perhaps an average CoC over a period of time ... but you are now getting into an exercise which is not entirely different than determining/projecting a rate of return :-)  Naturally the cash return is a component of overall rate of return."

Answer: Yes, depending upon the amount of the components that need to be removed.

@Emily RefiThe two common choices for investing retirement funds into real estate are the self-directed IRA and the Solo 401k.The Solo 401k requires self-employment activity, but will allow you to take participant loans while the IRA does not.A few other Solo 401k benefits: Compared to an IRA, Solo 401k contributions limits are roughly ten times higher.There is no custodial requirement for the 401k.You don't need the additional expense and administration of an LLC to have checkbook control.There is a built in-Roth component whereas IRAs are either traditional or Roth, not both.A spouse can also participate in the same Solo 401k plan.The Solo 401k has additional tax benefits over an IRA when investing into real estate using leverage.The penalties for prohibited transactions are less severe, though it's best not to utilize this benefit :)With either structure, it's generally recommended that you do not commingle retirement and non-retirement assets.