Devil in the details

Seasoned investors! 

My husband and I are wanting to do a house hacking strategy. We will use equity from our current house to purchase another to live in, with the intention of renting both of them out for retirement income/assets for our future kids to build their wealth off of. Im not sure down the line if we’ll continue this process, or expand our portolio to other investments. 

After doing some more research, I’m creating a checklist of  expenses/business management admin to prepare for. I want to know all of the small details to expect and plan for - not just the big picture plan. 

So far I'm looking into a financial advisor, estate planning attorney (thoughts on trust welcomed), operating and procuring under an LLC (advice welcomed on what type is best), reserves for repairs and vacancy, getting a home inspection on the current residence ahead of time to prevent unexpected repairs within reason/ or knowing what systems will be first priority replacement, each property having its own bank account, landlord home insurance, and talking to our CPA about what to expect on our taxes. We have a property manager we will use. Im also building out a vendor list for maintenance and repairs. We have already ran the numbers with our agent on rental comps and have an idea (no appraisal yet) on our current property value. The appreciation in our area is slower paced, but growing rapidly.

Basically, I want to go into the process well prepared and I’d love to hear where you think I should start, and ALL the nitty gritty details of investment property ownership. I dont want to miss a beat. I’d also love to hear what you personally look for in a property (age, location, size, etc.). The area we live in has little to no rentals within a 20 mile radius, so the demand is definitely there. 

Budget wise, we will not use all of our equity in our current property, only what’s needed. And a portion of it will be put in the reserves account to put us at least 6-12 months ahead, with the goal of keeping a years worth of rent in each property account, and the eventual small cash flow being put towards extra principal payments on our next property to build equity faster, and expedite the process of using the same strategy to eventually pay for building or buying our forever home. I'd love to hear thoughts on reserves as well. The home is about 10 years old, so after the inspection we should be able to gauge any repairs to expect. My husband is in construction so we also have some friends who can inspect systems  (roof, AC, plumbing, etc.) 

Tell me all the things please - my type B brain works better when I hear it from someone else, to organize my plan and thoughts! I am hoping to hear the worst of the worst so we aren't met with big surprises (as much as we can help it of course). For reference, I have a background previously being licensed in mortgage and as an agent so as far as lending and buying I'm covered in that department, so I'm looking to hear about ownership after the purchase.