For fix & flips and wholesaling, you'll need to network with seasoned investors and possibly even partner with them to learn the ropes.

You'll also need to consider ongoing costs like maintenance, taxes, and possibly financing. 

As soon as possible.

Hi Caroline,I had asked on a separate post if points on a rental property are tax-deductible in the year the property was purchased, and this is the answer I got:"Here's a general guideline:Points Paid for Acquisition of Rental Property: If you paid points to purchase your rental property, generally, you can deduct the entire amount of points in the year of purchase.

This definitely has revenue potential.The property also has other structures of value and amenities but these would not be part of the business described below.We will be able to add additional guest cabins and possibly our (retirement) home in the future.This is a rural area and about half of the property is AG-Exempt.

I want to create capital (I have some in my flip, future sale of my flip, possible HELOC on my primary, and investment acct) and I want to put it into cash flowing assets.

Here's a general guideline:Points Paid for Acquisition of Rental Property: If you paid points to purchase your rental property, generally, you can deduct the entire amount of points in the year of purchase.

This is absolutely possible.   

Possibly lower returns than projected because of statutorily mandated interest rates following court judgements. 

I think that whether a STR makes sense or not is entirely dependent on the market and that market's comfort and experience with STRs.