To gain the experience I need and to see how the hospitality world works for meI plan to continue airbnb arbritage for a bit until I can own my own property in the area but that will be some time from now as the average home price in the area is 600k+ I'd need to save atleast 15% (10% for down payment 5% for closing costs).

Rules/policies are subject to change and selling units in some buildings can be challenging.Condos, on the other hand, typically have more lenient rules/policies oftentimes allowing for unit owners to rent their apartments immediately and indefinitely.The rule flexibility, however, comes with a price.

If they do not qualify because of poor credit or income issues compared to being self employed etc there are differences - but typically people don’t qualify due to poor credit and people will seller finance to these borrowers thinking they woke up at a holiday inn and got a finance degree when in reality they repeat their past mistakesRemember the definition of insanity is doing the same thing over and over again expecting a different result

Timber you can let grow and it gains value. 

Typically, lenders don't look that hard into the LLCs.

And typically long term rentals don't make it easy to include property management fees into the numbers and have them still work well.I would consider looking into STR type areas where you can avoid the risk of property damages (str and pm insurance covers almost everything that they might damage) and evictions/collections.   

Essentially, instead of selling a property and paying taxes on the capital gains, you can reinvest the proceeds into a similar property and defer the taxes.

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

I had 3.5% rate, did a lot remodeling and heavy lifting, and decided to sell due to the 2/5 capital gains exclusion.

Is it a typical inn/bed and breakfast setup with all the rooms inside of a main house?