So from 2025, I’m thinking of living upstairs and running bottom floor (half of total RSF) as an STR.

if you asked the same question half of the folks would say they could live on 4 to 5k a month .. then it moved to 7 to 10 like you see today and by the time most folks are ready to really retire and I think that number will rise to 15 to 20k.

My insurance agent often does an adequate job.That sentance alone tells me I should shop around agents/providers, but what is the easiest/most effective way to do that?

Focus on these core concepts:Projected hold timeProjected cash-on-cash returnsProjected profits at the sale Projected Hold Time: ~5 YearsProjected hold time, perhaps the easiest concept, is the number of years we would hold the asset before selling it.

If I stop filling the bait stations, I will have a half dozen mice in the house within a month.

Easiest way to look at it. 

The backyard is fenced and on half an acre so that could be a big perk for dog lovers.

House-hacking a duplex/triplex/fourplex is one of the best/easiest ways to get your feet wet.

Normally the easiest and the least amount of documentation. 

I definitely want to meet Beth Johnson (already half way through her book and it's so fantastic) and pick her brain when appropriate.