If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

I have seen they have been pushing RentRedi a lot on the podcasts lately and I fell victim to their marketing tactics and checked them out.They seem to have fairly reasonable plans ($9/month for year plan) and offer a variety of features but I am still confused why someone would pay for property management software when there are so many free alternatives out there. 

Just noting that everything you wrote and have done so far is great - just be careful not to fall into the "analysis paralysis" trap and overthink before diving in! 

Ability to put deals together AND put them BACK together if/when they seem they'll fall apart. 

I agree with that, but I believe it's literally immediately for housing as in the first 1-12 weeks, and then falls it offs to the affordability angle and starts to close the gap on that.

Determining whether the venture falls under a service or rental business hinges on the provision of substantial services; for instance, if a bed and breakfast service is offered, it must be reported on Schedule C, triggering a 15.3% self-employment tax.Moreover, personal use plays a crucial role in the classification of the property.

AND you must maintain adequate reserves to take care of the disasters that may happen.So my advice- build your equity.Most of my clients fall into the first group above.

@Kevin Nichols You have to fall into their parameters just like any lender, but they're legitimate.

I’ll be moving to DC in the fall and will be living there for around 3 years.

I was on the phone with an owner yesterday who is contemplating selling, but will need to bring at least $150,000 to closing, due to the fact that their property is currently worth somewhat less than what they paid in...