All of my current rentals cost about the same to purchase ($215-265K), but cash flow is so different and current house prices are as well ($325-600K)...and the one I spent the most for and cash flows the most, is now the one worth the least (still worth more than I paid for it 3 years ago).

Most banks or lenders are looking for a property that has a LTV of 75% or lower after cash out and some requesting a DSCR of 1.00x once fully leased.If you was looking for $100,000 you would want to at least get the property to be appraised at $145,000 to get the most competitive pricing and enough cash out for yourself and closing costs.  

Take the highest rate and keep as much money in pocket as you can, even if you only breakeven when you refinance in the future (6 months) you can get your payments down, potentially roll in any costs, and skip a payment or two. 

I have a great management team ready to come in and operate this place the way it should be.

I don't think I need a service to do the billing as I'd just use my current management company, but I'm open to exploring this option if it makes more sense.  

Some lenders may want to see 6 months reserves on top of closing costs and downpayment. 6.

While there are costs associated with purchasing properties, the platform itself offers free access to property details and market data.

Next, what is the cost of the renovation vs higher rent delta? 

Our strategy is to buy land cash, take construction loan to build the structures.Some napkin math for this strategy:Land cost : $200,000Building and furnishing Cost: $400,000 for each A-frame (Provided we have electricity, well ready )Airdna revenue estimate shows $400 night rate with 70% occupancy.

Currently managing 2 short term rentals in Los Angeles.