After five years, you'll have earned $90,000 in rent income and gained $34,000 in appreciation.Buy four houses with $50,000 down on each.

Thank you for the feedback—it’s clear this discussion has helped me better articulate my goals and address the disconnect between my vision and the typical investor mindset.

@Austin TessMany lenders have a seasoning period (typically 6-12 months) before you can refinance.

Let's see: You sell one property, and to avoid paying cap gains tax, you then reinvest those profits within 45 days into a larger "like kind" property.

The sales comparison approach is typically done for residential real estate and will be less appropriate and come in under value because there are no good comps, and even an appraisal using the income approach (unless the appraiser is trained to do more complex commercial appraisals) is probably not going to be the most accurate either because they typically use market cap rates and in this case you don’t have good comparable income properties to find the market cap for the analysis.  

Major cities where STRs have only began rising up and gaining public spotlight with the rise of AirBNB are more likely to have more shifting and less stable regulatory environments since those areas are still in the process of trying to find the balance for STRs within their markets. 

For us we all typically use 0% business credit cards to furnish the property which can amount to $40-$60k+ depending on how crazy you go. 

Many houses that have gas only have 100 amp service vs the 200 amp that is typical of all electric homes.

@Jeff Shaver You can leverage your $550K equity by selling your San Diego property through a 1031 exchange to invest in a higher-cash-flow asset, like a multifamily complex, while deferring capital gains taxes.

It just feels like I’ve been making a lot of short term sacrifices for long term gains and I have to be really diligent with money management. or I could also just try to borrow money for the renovation, and pay off the line of credit over time, but I feel like that really would limit me and if the stock market(my collateral) went down I could also see some trouble.