Let's just imagine a scenario where you only have one property, and you don't use any PMSs or apps like Turno, for example.Cleaning and maintenance: 4 hours per weekRestocking supplies: 1 hour per weekResponding to inquiries and bookings: 2 hours per weekHandling guest concerns during stays: 1 hour per weekCreating and updating listings: 1 hour per weekManaging pricing: 1 hour per weekFinances and taxes: 2 hours per monthInspections and minor improvements: 4 hours per monthTotal estimated time per week: 12 hours, more or lessTotal estimated time per month: 26 hours, more or lessIf you do use pieces of software to automate your work, it can be even less.

@Zachary JensenIs it only depriciation or also insurance/re tax/mortgage costs?

He narrowly escaped the property tax sale on his primary home a few weeks ago.  

New Home: I would need to dump some of my brokerage accounts for the downpayment(so some capital gains taxes would need to be paid to finance the downpayment on the new house) or if I sold our "current residence(2nd home)" I wouldn't need to.I understand the tax incentive of selling within 5 years of living there for 2 years, however, the cash flow seems larger then what I would get taking the money and investing in new RE in the future. 

I work with a handful of investor friendly lenders that don't require W2s or tax returns (lending is based on the property not the borrower) but am always exploring new avenues.

Does that include taxes and insurance? 

Otherwise you will have to pay higher rental mortgage rate.4) If all goes well, you buy your new home to live in with FHA 3% down or FNMA 5%+ down and rent out unit you were living in. 5) Yes, you may have negative cashflow on the rental for the next 1-3 years, until rents increase, but this is part of investing.Be sure to calculate any changes in the rental property taxes and home insurance resulting from you moving out.

They designed a very nice postcard for me and i sampled a batch of about 1500 postcards to a list I provided to them.My results....7 responses (0.46%).The list was Out-of-State owners I pulled from the tax records, of which I got about a 13% response rate using yellow letters.I'm not going to say anything bad about them, I just don't think postcards work well for finding motivated sellers in my area.

You should certainly start the process earlier than maturity, especially at the very least within a couple months of the maturity date - there can always be things that cause delays and pushes and even missing the maturity date by a couple weeks can have harmful consequences (since it will technically be a default / missed payment even if the lender is OK with it).Also, commercial loans even with the strictest prepayment protections / lockout periods will almost always have at least a 3-month open period prior to the Maturity Date

The taxes on this property according to the listing is $15,000.