I don’t believe you need to allocate more for a STR compared to a LTR, but should consider the life of the property and what expensive items might need to be replaced/age of these items such as the furnace, A/C, roof, water heater etc.

You'll have a much lower chance of any crazy expensive roof/HVAC issues for a while (knock wood), and that will give the rental market time to catch up.

The problem you have is; if you really want to know how well the heating and cooling system is, and the condition of the roof, plumbing and electrical system then you need to hire a plumber, electrician and roofer because believe it or not general contractors do not specialize in those trades unless they have a license specific for each or any of those trades.The problem I run into when calling contractor for inspections is I get a lot of b.s..

So long story short, in the past 1.5 years, we have renovated 9 of the 24 units, installed new roofs on 3 of the 6 buildings (this was known at purchase), and replaced 8 HVAC systems. 

I also don’t think I’d be a bad agent at all, and the entrepreneurial aspect (scalability, no boss, high commission, hard work=better pay) all appeals to me.

Insurance rates are through the roof due to cost of material they say.

I need to have my roof inspected and it is possible it is time for a replacement at my property in Austin.

The property is in need of heavy renovations (repair a brick wall that partially fell/collapsed, new roof, etc.).

Tile roof, stucco siding, no weather events and 20 year old housing stock makes a big difference. 

Solid mechanicals, solid roof, foundation in great shape, everything you could want in a building... they tried to sell it for a decade and received exactly 0 offers.