Cash flow of approximately $340/month.

I hope you got an inspection contingency clause put into the P&S agreement as you could still back out if more problems come up in the inspectionNow the cash-out refi could work but that would require you to rent out the property for at least 6 months and pay closing costs again and now that the home is worth more you would have to make sure you will cash flow because everything from the taxes to the mortgage payment will be more per monthWith this being said the profit is there if everything with the comps are correct so I would say if you feel comfortable with it to go with that route.I also now am seeing this is a 3-month-old post so if it is going well then congrats if not then you will get'em next time (hopefully not losing money in the process) but if you didn't do the deal out of fear then I would say hit the books again (aka laptop) and get to studying and learning about all of your fears to see if more knowledge can combat those fearsHope this helps, good luck :)

Want to keep it, but when I account for all expenses the cash flow is really rough.

Only issue might be the budget.I think the two main questions I’m trying to answer for now are: 1) Do I want to do short term rentals to increase chase flows or long term so it’s a bit less day-to-day work?

It could be worth the consideration to start helping sell like-properties to investors doing the type of investing you are interested in and learning the process in the meantime, getting paid to do so

When we buy we always require the deal to pencil with positive cash flow of about $300/month for the kind of houses we like.If I had a property that was not cash flowing I would seriously consider doing a 1031 exchange to get into one that does cash flow.

depends on so many things, but a start to think throughCash Flow Structure:Operating Company to Holding Company: This is a common setup where the operating company (property) generates rent and pays it to the holding company.

Here is how to buy using "off market", "Subject To" and save $410,755 on the same property.
Notice that the purchase price is less for the same property, because the seller is selling for what they owe on it. This is...

It will cash flow about $800 after refinance.

So there is no consideration of what type of financing you are using.They may be concerned with the period leading up to closing and making sure that you can qualify etc.