Most bookkeepers won’t work in it if you plan to outsource it in the future.

As RE developers we all know how important it is to hire good, reliable residential contractors. 

Most importantly, I'm sure you would agree, this has been a huge learning experience that will allow you to be a more successful & savvy investor in the future based on this experience. 

- How many below-asking price offers will they write for you before ignoring you?

Very exciting you are looking to get into the RE investing world.Thanks for the interest in Rent To Retirement.

If you don't plan on allowing 4+ cats in your rental in the future you shouldn't start now.

@Tanner KingWhen I analyze a house hack deal, I focus on metrics like GRM, Cap Rate, Cash Flow, House Hack Savings, and Future Rent Potential.

Future land appreciation in this area might outweigh any tax benefits from buying in other areas, with a better (tax-wise) ratio.Before pursuing your plan, talk to a real estate accountant to figure out if you can, in fact, benefit from cost segregation.

However, you can defer taxes under §1033 involuntary conversion if you elect to reinvest the proceeds into a similar rental property within two years (three years if the government condemns the property or threatens to do so, and four years for a principal residence in a federally declared disaster area).To reduce taxable gain, consider:Electing §1033 treatment and reinvesting the full $300K into a new rental property to defer taxes completely.Partial reinvestment, where only the portion not reinvested is taxable.Properly documenting all replacement costs and property details to ensure IRS compliance.Using cost segregation on the new property to accelerate depreciation and offset future taxable income.Since the §1033 election must be made, consult a tax professional to ensure compliance and maximize deferral benefits.This post does not create a CPA-Client relationship.

A lot of my friends started RE investing that way.