All Forum Posts by: Matt Mainini

Thank you all for thoughtful responses.  I agree with these possibilities, and unfortunately I hoped for a new approach in which I can work with them and grease the wheels to get the result I want, but you are basically just saying move on, which is easier in the end.  I hate wasting time but going through contractors is how it is, I suppose.

I am really surprised and caught off-guard by this.  Over the last 2 years that I've managed a short-term rental in northern San Antonio, I have experienced many small contractors that get so easily triggered, offended, and upset at me and my wife.  My wife is a soft-spoken 5'2" asian lady.  She is the least intimidating person ever.  This is in sharp contrast to our properties near Santa Cruz, California, where we spend most of our time and energy.

Californian's are known to be laid back and soft compared to east-coasters.  I don't know about Texas.  I believe that we're being very kind, fair, friendly, respectful...you name it.  I'm not new in this space and know how to build long-lasting relationships over many years.

Is there something I'm missing about the dynamics of hiring smaller contractors (handyman, landscaping, etc) in San Antonio?  Are they eating a little too well right now?  Are they supposed to be "the expert" and "have all the answers" rather than work it out with an investor?  I mean, I'd like to discuss how the project will be performed in a general way - and I think my questions about how they will perform the work are offending them.  As if I'm supposed to know nothing, and just rely on them 100% without questions or requests.  

So far the tally must be something like 40% of them go sour really quickly.  In CA, I don't recall a single one, which I have had many many more interactions with contractors over the years.  What is up with San Antonio?!  Or, is it ME!?

I'm finding a lot of interest from Craigslist - not sure if the candidates will be qualified but at least I'm getting interest! :)

I am seeking a "runner" or someone to check on my property between guest stays.  Any suggestions for finding a solid individual or company to help manage a short term rental?  I'm also looking for handymen to make minor repairs.

Thanks!

Great information, thanks Jonathan.  Also keep in mind your septic may pass inspection in the summer when you buy your property, then actually fail in the winter rains.  Some of us have learned the hard way!

With one of the largest expenses on the line, I suggest the buyer truly understand the septic's health, not simply hope to pass the inspection.  You really need to learn your septics operational health, which is difficult given that it's completely underground!  There are many different ways to test and inspect.  Don't trust just one random inspector opinion.  Get a lot of eyes on it if you're unfamiliar with your system. 

If cashflow was the requirement for any investment, the Santa Cruz market would stop moving.  Or, the only buyers are from oversees with cash, which we see in this area.  Very few deals are going to cash flow right away.  Where do the rest of us fit in then?  If you're not familiar with the area, which is one of the the least affordable places in the US to live, then it may be difficult to understand Dax's perspective. Often, "breaking even" means principle paydown of roughly $1,000 to $2,000 per month. How many doors in the midwest are required to earn that? So on a typical SFR, if you're breaking even, you're making quite a bit of money over time, albeit with the risks we know exist when the property is not cash flowing. So it is harder, and you need to be even more prepared in such an environment. But I also agree with Dax, just holding onto property is a huge win in this market, and over time the wealth is greater than many other safer markets.

Well said, Dax!  Thank you for sharing!  Any thoughts on commercial multi-family specifically?

We're looking to expand into the San Antonio short term rental (STR) market and I would like to network and discuss anything related to the neighborhoods and your experience with San Antonio real estate. Currently I own long term rentals in other states and very interested in investing in San Antonio.

I'm serious and ready to buy.  Having fun!  Please reach out if you're an agent, property manager, or fellow investor - I would love to chat about your goals in real estate and support each other.

@Ashish Acharya and @Basit Siddiqi

Thank you for your insights.  If the seller goes beyond 5 years (meaning, they no longer lived in it for 2 years), they must pay capital gains (such as 20% on 500k gain = 100k).  So, in that event, taxes must be paid on the gain at any point in the future right?  So if you don't sell within the window, to make the same 500k net gains you would have to wait for the appreciation and cash flow to grow larger (is it about 620k gain?).  Instead of 500k no tax scenario, you would need more like 620k as the entire amount will be taxed at 20%. If I wait too long and miss out on tax-free sale, how long until I would net the same?  Let's assume the full 500k in gains for a married couple.

What was the answer @John Emmerich?  I'm in a very similar position, and have 6 months left before I cross beyond the 5 year mark.  We have lived in the property 2 out of the previous 5 years.  I have potentially big gains if I sell, so wondering what my situation would be if I wait beyond the "pay no capital gains" benefit.  Would I have to wait for appreciation/cash flow to grow, offsetting the taxes I would pay at the time of sale?