The residents do not cause problems, they are generally on social security so if you give them a 5% discount they will pay their rent a year in advance, and they will host fundraisers to improve "their" clubhouse.

We allow guests to pay 50% at time of booking on the Airbnb platform.

So far this year from MLS data, in Dane County, the median 3 bed, 2 bath home sold for $440k and $429,950, so with our high taxes (around 2% of the purchase price), you may decide to focus on multi-family property for help with income/cash flow. 

DSCR is calculated by using the monthly market rent or lease (up to 120%) and dividing it by the Principal, Interest, Taxes and Insurance Payment. 2.

Plus with HELOC's you can only pull what you actually need and pay it down/pull the cash out as you need it.

As long as I keep track of what expenses belong to which LLC, is it safe to continue running all of the payments and credit cards through the holdings company and then just divvy it up during tax time?

Some investors think I am crazy doing that and perhaps so, but I take other people's money seriously and even when the crap hits the fan (and it will if you do enough deals for a long enough period of time), paying back your lender is priority one in my book.Most of my deals for private money also include a balloon payment rather than monthly payments.

Were you there 2 of 5 years for tax exemption?  

I purchased a townhome last year in Nevada & I have tenants who are paying off the mortgage. 

Also, with point 4 - is 18 months not a very short window to pay down the cost of a home?