I suppose in the long run it would still be worth it, but it seems difficult to swallow the fact that I’d be “losing” money for awhile instead I making it! 

Im sure the cost is a hard pill to swallow but try and keep your eye on the long term prize of making $ on a thriving STR biz.

So, 400k - 500k sounds like lots of money but if you wanna operate in the 300k+ entry point it get can swallowed up quick.One strategy I'd try is to be a buyer at the auctions, win a bid on a good house, close on it in cash (you should be a great deal under market value) and then get into a delayed purchase bridge loan product which will cash you out a certain percentage of the purchase and supply the rehab funds. 

So much of the land was just taken by the river anyway -- it just re-routed itself and swallowed up most of the land on the riverside of the road.I do have one more favor to ask -- if anyone has leads on an accountant that can jump in to help us file last year's taxes by late November, I would be grateful to hear -- I still need to get them done, and especially need them done in order to apply for the SBA loan by the December 2 deadline.

It may be a tough rate for you to swallow, but it may be worth it to secure the properties then refinance in a few years.

So you can say I was naive but I calculated that if this was a loss, its a loss I can swallow and move on.

@Jay Hinrichs I love your honesty through the entire 30 pages,  a hard pill for many to swallow but I get you my man, and would love to connect with you . 

Having a hard time to find anything remotely comparable to this home in CAHowever being a remote landlord feels like a tough pill to swallow hence the confusion. 

With that being said, asking for advice and following the counsel of more seasoned individuals should not be overlooked.After walking the property with local well seasoned contractor, with plans in hand I had to swallow my pride and fixation on what I am hoping to accomplish and start with the basics.

Tough pill to swallow, I like cash and certainty over sub2 all day but that's my preference.