Likely more than most brrrr, but with an ideal brrrr I can make infinite return.  

Each property ideally has its own business bank account, as well as your master LLC.Question, is the master LLC acting as the property manager for the other properties?

Also, my insurance company said it would be the same rate regardless which option I go with.or do I stick with the cheapest option upfront like a shingle roofObviously the upfront cost/future cash flow will be hurt the most by the standing seam steal roof (although it could assist in resale value)Does anyone have experience on roofing or an opinion which is most ideal for this scenario?

@Nevin WilkieLuxury Vinyl Plank (LVP): Durable and hardwood-like, LVP is ideal for rentals or flips.

FHA loans with low down payments are ideal for this.In the meantime, focus on improving your credit score and maintaining a solid financial foundation.

The property is unique so you would do well with families who also need to WFH so insurance displacement would be ideal.

My ideal is to have a system or a standard in place to maintain discipline about procedures.

Ideally you are exceeding the AirDNA numbers but it can be a good gut check on average rates/occupancy for that specific neighborhood, etc

That sounds like an ideal situation versus doing a full fix and flip for your first deal. 

You could get the DSCR on first and if your bank allows it do a second position HELOC on the investment property (this would be pretty rare if a bank allows this) but putting DSCR on second would not be ideal.