STR PotentialWith $40K in annual revenue, reaching $1,000/month in cash flow will require some adjustments.

Higher down payments, adjustable rates, but it would allow you to leverage instead of paying all cash.

what is the benefit of putting a new STR into service towards the end of the year vs the beginning of the next year?

If your adjusted gross income (AGI) exceeds $150K and you are not classified as a real estate professional, passive losses from rental properties cannot be used to offset your earned income.

Well, if the FMV of the house is at or near $300k based on reasonable comps, and there's no legitimate benefit to the client's offer (i.e. all cash, fast closing, no contingency, whatever), I'd probably quit working with them because there's really little to gain working with cheapskates and bums who just want to steal other people's property.

I went through the initial 2 months having to fix even the most minor of issues that other tenants would normally be very adjusting.

If so then you should have a serious conversation with your cpa to figure out the tax benefits of pursuing one strategy over another?  

Many banks handling tax escrow accounts for mortgages have mistakenly thought there was one tax due twice/year or totally missed one of the taxes.Investors should research the SEV and the Non-Homestead property tax millage rates to project what the property taxes will be after adjustment.

You're already thinking about long-term benefits, and it's great that you're bringing your contractor husband's expertise into the equation.To alleviate some of the stress, I recommend starting by focusing on quality properties in solid areas where you can add value.

They presented a juicy case study to illustrate the benefit of depreciation recapture shifting from cost-segregated personal property to real property.