One of the things I'm trying to figure out is if I'm better off getting a few lower cost properties or on higher priced property. 

Using a HELOC to fund your first rental can be a great strategy, especially if you want to preserve your cash for other expenses or unexpected costs.

Time and practice will still teach you as you do deals but it will help you understand what things costs for the size of the property 

Most likely your insurance deductible will be more than that and an attorney will definitely cost you more than that.

The end product will be great, as others have mentioned perhaps in other threads, Delta has not increased any of the cost, so there is still a huge equity upside.

Thanks Shannon  Does it cost less to go straight through WAIVO? 

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

We are looking towards STRs in order to lower our W-2 taxable income via cost seg and bonus depreciation.I believe my line of work qualifies me as a REP, but what I am not clear on is whether I would still need to meet the 'material participation' requirements in our rental business in order for our losses to be non-passive.

On your tax return you would report the proceeds, subtract costs and proceeds paid to seller, then the remaining profit would be your flat fee.

The market between the 2 locations & resident class (Especially if you plan to self mange or find a PM company), Your future goals and the costs associated with moving and transferring to a new hospital.