This is where you can significantly increase the value of the property by making improvements that attract quality tenants and justify a higher rental price.

All my experiences on Booking.com have been good people at high profit.

In a climate like this with high rates, probably better to use a Heloc so you keep the lower rate of your 1st lien.

Again, this is due to how long it was taking to get work done, the quality and lack of communication (I'm happy to post examples as well), and frankly, the quality of work expected once I realized how many things I was not told about before the purchase.However, you did not offer in any way to address issues left by the prior tenant and made it clear that it was my responsibility.

And DIY repairs are not recommended for other reasons: it will take you much longer to complete, depriving you of rental income, and you run a high risk of your wife becoming your ex-wife.Same risk exists if you push your wife into becoming a Realtor or some other real estate activity just for the sake of tax benefits.

You have a lot going on and if you had a 457 you were a highly compensated EE.   

and you will have many many applicants assuming the quality of the rental and the rents requested.  

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

This would depend on if you used a high interest rate hard money loan for the purchase of the property. 

But the level of negative cash flow that you're talking about is quite high and it sounds like it's not something you're comfortable with and thus should look for something else.