File Bankruptcy and fix your house up and sell it or sell it as is for the amount you said it was worth vs what you have it under contract for now.  4.

Considering the high deductible on House B, I am only filing a claim for House A, and coming out of pocket for the cost of repairing or replacing the roof for House B. 

If you expect a large tax balance this is why people rush to get it into services ASAPEdit: To also add if the taxpayer qualifies for the "STR loophole" as some call it, even if they don't have much rental income, they could use the losses produced by that STR to offset other income.

Here's a link to the bill: https://beachrentals.penfedrealty.com/sites/default/files/ar...  

It contains hundreds of files such as ebooks, checklists and spreadsheets for real estate investors: https://www.biggerpockets.com/filesGood luck.

This amounts to lost opportunity because if you had purchased RE, at the closing it can start producing return. 5) ADUs detract from the existing structure whether this is privacy, a garage, or just yard space. 6) this is related to number 1, but there are many more buyers looking to purchase homes for their family than there are RE investors looking to purchase small unit count properties.

A property qualifies as Homestead for this exemption if an eligible owner files a Principal Residence Exemption (PRE): https://www.michigan.gov/taxes/0,4676,7-238-43535_43539-210891--,00.html#:~:text=Section%20211.7cc%20and%20211.7,purposes%20up%20to%2018%20mills.Many investors have gotten an ugly surprise when they bought a property that was a primary residence of the seller for the last 20 years.

Plus if you bought with all cash from the proceeds of the sale you would be trading down in asset value quite a bit.Depending on the refi rate you could consider keeping this and refinancing it to pull some cash out which you could use as a down payment on another property.Just some thoughts, hope they help the issue with the refi is those rates at the new loan if i do a 75% LTV will almost overcome the cash flow its producing now and basically get to a break even point.

If it is way more work and maintenance but cash flowing the same as a smaller unit doesn't make sense, but since you say high maintenance high reward I'm guessing this is one of the best producing properties.  

Very likely the seller doesn't know the income-producing value of those extra spaces and therefore has not included it in their pricing.