I am looking into purchasing a second (vacation) home and would love to hear your thought on the pros and cons of going a conventional 30-year second mortgage vs. using a HELOC or Home Equity Loan on my Primary Residence to purchase the second home outright. 

Purchase price: $205,000 Cash invested: $60,000 This was the first property I purchased.

Regular home purchase or sale?

I work with out-of-state investors and would be happy to share my experience and how I can help you in your next investment purchase.

So it does appear to be possible to get an FHA 203k loan for a 5-unit & convert to a 4-unit.When possible, aim for the Limited (aka Streamline) 203k loan, as it's less complex, not required to get an FHA consultant, etc.Of course, this is based of the two following important assumptions:1)  zoning allows for this2)  and obviously I owner occupy for at least 12 months3)  the total purchase price + renovations are within the FHA loan limits specific to my areaWhat I'm confused about is the timeline or chronological order of the process? 

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

Part of rent is applied to purchase price. 

I purchased a property that needed a lot more work then intended.

I have experience as a Residential agent in Denver, CO and as a commercial Leasing Associate in Chicago, IL.I am planning to purchase my first rental home here in the next year or so and make it my primary residence.

Purchase price: $178,000 Cash invested: $10,000 primary home own use has an Airbnb/ short term rental 5 months out the year/sometime this year will try BRRRR