It'll be up to the next generation to figure out if they want to build an empire or not. 

I like the idea of STR as it seems like it can generate significantly more income than LTR and would allow me to block out dates if I have friends or family come visit.

Direct bookings results in higher revenue.  

This either sounds like a seller looking to "retire" and liquidate his holdings or a Section 8 owner that hasn't kept the property (or rents) up to market levels.So, based on the numbers you're using, what return (IRR, Equity Multiple, or ConC) are you estimating you'll generate over your expected holding period?

The Numbers:Cash Flow Analysis: Investors typically look for properties that will generate positive cash flow—meaning the income from rent covers the property’s expenses (mortgage, taxes, maintenance, etc.) and then some.

Issue:  computer-generated random phone numbers for outgoing calls. 

The additional cash you have due to leverage put into more hard assets and the cash flow generated put into fixed income/equities after reserves.

Now this is an annual thing (for all new properties).For rough math, you can generate a tax write off about 15-20% of the real estate value: one a million you can expect a $150k to 200k write-offs.

Quote from @Theresa Holl: Quote from @Varinder Saini: We are building a real estate AI platform that specializes in analyzing disclosure packets of hundreds of pages and generating concise single report of important findings. 

You make revenue here and there but the goal is to generate enough in the winter to sustain all the expenses for the entire year.