It's maddening that he could've built so much equity in the past 15 years but he's been on the wrong end of the equation due to that anxiety about making the plunge.

You can also use “Buy Nothing …”, thrift shops, etc to reduce cost but these options often take more effort and time (but a great find on Buy Nothing feels great).The average SFH (I recognize yours is a duplex and not SFH) LTR rent increased $700/month in San Diego in the last year.  

Yes, the flow through is reduced by $100k but it will be reflected in the employee's W2.Therefore, the W2 wages is included in the employees wages, hence paying income taxes and the Company paying the 15.3% payroll taxes.

As time goes on, I'm sure you'll refine your process to reduce guest issues and your cashflow will only get better.

Simply enter some information to view projected key return on investment (ROI) metrics, including cash flow, cash-on-cash return, net operating income, and cap rate.Minimize risk by investing in a pre-inspected, turnkey rental property with a tenant in place to earn cash flow beginning the day the deal closesBegin the loan application process early, because sometimes lenders require more paperwork than when you’re financing in your home stateHire a good local property manager who has experience working with out of state investorsWhile buying out of state rental property does come with some risk, investing the right way helps to minimize those risk while maximizing the overall returns of your property portfolio:Key reasons for investing out of state include increasing cash flow and portfolio diversification.Affordability, matching markets with investment strategy, and property affordability are three advantages to buying real estate out of state.Turnkey rental property and a local property manager help to reduce the risk of investing outside of your home state.All the best!

Do you have many restrictions (no pets, etc) which reduce your guest/tenant pool? 

The goal here is to significantly reduce one of the largest expenses for many people- housing.

It reduces your risks in finding deals. 

I try to use my business credit and reduce what I hold in my personal name.

You also have to understand this is still a peak market with a good chance that property values will decline 10% or more in the next 12 months and a lot of people jumped into the short-term rental market during the last two years, so this may reduce the demand and potential income.1.