Every week, we hear about another city devastated by a natural disaster.

Licensed with permits ~$3,250.HWT standard gas single family low efficiency without exhaust retrofit $900.Sand and stain hardwood floors, natural stain $3 per sf.Paint interior walls, ceiling trim and doors 3 tone paint scheme 2 coats $3.20 per sf (floor area cost includes paint)Click lock LVT flooring install overlay inclusive of prep and quarter round $4.50 per sf (materials and labor)Asphalt roof installation 3/1 - 800 sf bungalow with 2 layers of shingles - ~$7,900Standard porch cap replacement with 2 new precast concrete steps ~$2,500Used stove or refrigerator delivery and install $350New stove or refrigerator delivery and install $HD model specificUse this as a general guideline. 

Your examples of tenant evictions, contractor management, and neighbor complaints truly illustrate the hands-on nature of this business.I'm particularly interested in your experience and was wondering if you might be willing to share a specific instance where you faced a particularly significant, "make-or-break" challenge in your real estate journey.

Quote from @Stephen Morales: Hey Jared, I would suggest picking up properties with value-add opportunities.

With $400k available to me, I have a market picked out already, that will allow me to buy 2 LTRs, about $200k down each, that will cashflow a little over $1000 a month combined. 

Mother Nature-  just have to deal with.

(I have experience raising money as a professional musician so this came somewhat naturally to me). 

If you’ve got experience in this space, I’d love to pick your brain on best practices, biggest mistakes to avoid, and strategies for finding profitable deals.

Tenants, "go into Holiday-mode" and start spending disposable income (and racking up their credit cards) on Thanksgiving feasts & trips, Xmas presents & trips, and finally NYE plans.3) Income Tax Refund checks start being received towards the end of February and corresponding, the rental market starts picking up again as tenants payoff their “Holiday Hangovers".4) Spring Fever starts, sometime in April-May, causing both sales & rental markets to start picking up.

Look, I'm a real estate agent - so I naturally love to buy/sell homes, but that doesn't mean it's always the alpha investment at any given time for your particular circumstances.Congratulations on your family and all that you guys have accomplished so far!